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Sample records for alkyl cycloalkyl phenyl

  1. Multipotent MAO and cholinesterase inhibitors for the treatment of Alzheimer's disease: synthesis, pharmacological analysis and molecular modeling of heterocyclic substituted alkyl and cycloalkyl propargyl amine.

    PubMed

    Samadi, Abdelouahid; de los Ríos, Cristóbal; Bolea, Irene; Chioua, Mourad; Iriepa, Isabel; Moraleda, Ignacio; Bartolini, Manuela; Andrisano, Vincenza; Gálvez, Enrique; Valderas, Carolina; Unzeta, Mercedes; Marco-Contelles, José

    2012-06-01

    The synthesis, pharmacological evaluation and molecular modeling of heterocyclic substituted alkyl and cycloalkyl propargyl amines 1-7 of type I, and 9-12 of type II, designed as multipotent inhibitors able to simultaneously inhibit monoamine oxidases (MAO-A/B) as well as cholinesterase (AChE/BuChE) enzymes, as potential drugs for the treatment of Alzheimer's disease, are described. Indole derivatives 1-7 of type I are well known MAO inhibitors whose capacity to inhibit AChE and BuChE was here investigated for the first time. As a result, compound 7 was identified as a MAO-B inhibitor (IC(50) = 31 ± 2 nM) and a moderately selective eqBuChE inhibitor (IC(50) = 4.7 ± 0.2 μM). Conversely, the new and readily available 5-amino-7-(prop-2-yn-1-yl)-6,7,8,9-tetrahydropyrido[2,3-b][1,6]naphthyridine derivatives 9-13 of type II are poor MAO inhibitors, but showed AChE selective inhibition, compound 12 being the most attractive as it acts as a non-competitive inhibitor on EeAChE (IC(50) = 25 ± 3 nM, K(i) = 65 nM). The ability of this compound to interact with the AChE peripheral binding site was confirmed by kinetic studies and by molecular modeling investigation. Studies on human ChEs confirmed that 12 is a selective AChE inhibitor with inhibitory potency in the submicromolar range. Moreover, in agreement with its mode of action, 12 was shown to be able to inhibit Aβ aggregation induced by hAChE by 30.6%.

  2. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 1,4-Benzenediamine, Nâ²-(alkyl)-N- phenyl]-N-phenyl- (generic). 721.10349 Section 721.10349 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N-...

  3. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 1,4-Benzenediamine, Nâ²-(alkyl)-N- phenyl]-N-phenyl- (generic). 721.10349 Section 721.10349 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N-...

  4. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 1,4-Benzenediamine, Nâ²-(alkyl)-N- phenyl]-N-phenyl- (generic). 721.10349 Section 721.10349 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N-...

  5. Surfactant composition containing alkylated biphenylyl phenyl ether sulfonates

    SciTech Connect

    Hinkamp, P. E.

    1984-09-04

    The title compounds are of the formula (R)Y, (((R)X,(M(+)(-)O35-)A-Phenyl)-), (((R)Z, (M (+)(-)O35-)C-Phenyl)-O-)Benzene R is an alkyl radical of at least 6 carbon atoms and each R can be the same or different; M(+) is hydrogen, alkali metal ion, alkaline earth metal ion or ammonium ion radical and each M(+) can be the same or different; a, b and c are individually integers of 0 or 1 with the proviso that the ..sigma..(a+b+c) is equal to 2 or 3; and x, y and z are individually integers of 0-2 with the proviso that ..sigma..(x+y+z)greater than or equal to1. These compounds demonstrate good tolerance to multivalent cations, such as the cations of calcium and magnesium, good resistance to hydrolysis and are useful surfactants in enhanced oil recovery processes.

  6. Organophosphazenes. 18. Friedel-Crafts Phenylation Reactions of Alkyl and Nimethylamino Fluorocyclotriphosphazenes.

    DTIC Science & Technology

    1984-11-15

    ag, o.. a RIM COMAS.,A, Organophosphazenes, 18 . Friedel-Crafts Technical Report Phenylation Reactions of Alkyl and Nimethylaming...Organophosphatenes. 18 . Frliedel-Crafts Phenylation Reactions of Alkyl and Dimethylauino Fluorocyclotriphoaphazenes Christopher Wf. Allen, Scott...intensities were .................. .... . - ..-...--. - . . * -..-....- °.- 6 corrected accordingly. The structure was solved by direct methods (MULTAN80) 18

  7. Inhibition of carbonyl reductase activity in pig heart by alkyl phenyl ketones.

    PubMed

    Imamura, Yorishige; Narumi, Rika; Shimada, Hideaki

    2007-02-01

    The inhibitory effects of alkyl phenyl ketones on carbonyl reductase activity were examined in pig heart. In this study, carbonyl reductase activity was estimated as the ability to reduce 4-benzoylpyridine to S(-)-alpha-phenyl-4-pyridylmethanol in the cytosolic fraction from pig heart (pig heart cytosol). The order of their inhibitory potencies was hexanophenone > valerophenone > heptanophenone > butyrophenone > propiophenone. The inhibitory potencies of acetophenone and nonanophenone were much lower. A significant relationship was observed between Vmax/Km values for the reduction of alkyl phenyl ketones and their inhibitory potencies for carbonyl reductase activity in pig heart cytosol. Furthermore, hexanophenone was a competitive inhibitor for the enzyme activity. These results indicate that several alkyl phenyl ketones including hexanophenone inhibit carbonyl reductase activity in pig heart cytosol, by acting as substrate inhibitors.

  8. 40 CFR 721.9530 - Bis(2,2,6,6-tetra-methyl-piper-idinyl) ester of cycloalkyl spir-o-ke-tal.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...) ester of cycloalkyl spir-o-ke-tal. 721.9530 Section 721.9530 Protection of Environment ENVIRONMENTAL... of cycloalkyl spir-o-ke-tal. (a) Chemical substance and significant new uses subject to reporting. (1...-clo-alkyl spir-o-ke-tal (PMN P-88-0083) is subject to reporting under this section for the...

  9. pi-Selective stationary phases: (II) Adsorption behavior of substituted aromatic compounds on n-alkyl-phenyl stationary phases

    SciTech Connect

    Gritti, Fabrice; Guiochon, Georges A; Mayfield, Kirsty; Dennis, Gary; Shalliker, R. Andrew

    2010-01-01

    The frontal analysis method was used to measure the adsorption isotherms of phenol, 4-chlorophenol, p-cresol, 4-methoxyphenol and caffeine on a series of columns packed with home-made alkyl-phenyl bonded silica particles. These ligands consist of a phenyl ring tethered to the silica support via a carbon chain of length ranging from 0 to 4 atoms. The adsorption isotherm models that fit best to the data account for solute-solute interactions that are likely caused by p-p interactions occurring between aromatic compounds and the phenyl group of the ligand. These interactions are the dominant factor responsible for the separation of low molecular weight aromatic compounds on these phenyl-type stationary phases. The saturation capacities depend on whether the spacer of the ligands have an even or an odd number of carbon atoms, with the even alkyl chain lengths having a greater saturation capacity than the odd alkyl chain lengths. The trends in the adsorption equilibrium constant are also significantly different for the even and the odd chain length ligands.

  10. Design and synthesis of some new 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-ureas as potent anticonvulsant and antidepressant agents.

    PubMed

    Mishra, Chandra Bhushan; Kumari, Shikha; Tiwari, Manisha

    2016-05-01

    A series of 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-urea derivatives (29-42) were designed, synthesized and evaluated for their anticonvulsant activity by using maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) seizure tests. The acute neurotoxicity was checked by rotarod assay. Most of the test compounds were found effective in both seizure tests. Compound 30 (1-{4-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-urea) exhibited marked anticonvulsant activity in MES as well as scPTZ tests. The phase II anticonvulsant quantification study of compound 30 indicates the ED50 value of 28.5 mg/kg against MES induced seizures. In addition, this compound also showed considerable protection against pilocarpine induced status epilepticus in rats. Seizures induced by 3-mercaptopropionic acid model and thiosemicarbazide were significantly attenuated by compound 30, which suggested its broad spectrum of anticonvulsant activity. Interestingly, compound 30 displayed better antidepressant activity than standard drug fluoxetine. Moreover, compound 30 appeared as a non-toxic chemical entity in sub-acute toxicity studies.

  11. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  12. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  13. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  14. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  15. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  16. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  17. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  18. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  19. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  20. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  1. Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides.

    PubMed

    Daifuku, Stephanie L; Kneebone, Jared L; Snyder, Benjamin E R; Neidig, Michael L

    2015-09-09

    While previous studies have identified FeMes2(SciOPP) as the active catalyst species in iron-SciOPP catalyzed Kumada cross-coupling of mesitylmagnesium bromide and primary alkyl halides, the active catalyst species in cross-couplings with phenyl nucleophiles, where low valent iron species might be prevalent due to accessible reductive elimination pathways, remains undefined. In the present study, in situ Mössbauer and magnetic circular dichroism spectroscopic studies combined with inorganic syntheses and reaction studies are employed to evaluate the in situ formed iron species and identify the active catalytic species in iron-SciOPP catalyzed Suzuki-Miyaura and Kumada cross-couplings of phenyl nucleophiles and secondary alkyl halides. While reductive elimination to form Fe(η(6)-biphenyl)(SciOPP) occurs upon reaction of FeCl2(SciOPP) with phenyl nucleophiles, this iron(0) species is not found to be kinetically competent for catalysis. Importantly, mono- and bis-phenylated iron(II)-SciOPP species that form prior to reductive elimination are identified, where both species are found to be reactive toward electrophile at catalytically relevant rates. The higher selectivity toward the formation of cross-coupled product observed for the monophenylated species combined with the undertransmetalated nature of the in situ iron species in both Kumada and Suzuki-Miyaura reactions indicates that Fe(Ph)X(SciOPP) (X = Br, Cl) is the predominant reactive species in cross-coupling. Overall, these studies demonstrate that low-valent iron is not required for the generation of highly reactive species for effective aryl-alkyl cross-couplings.

  2. Design, synthesis, antioxidant, and anti-breast cancer activities of novel diethyl(alkyl/aryl/heteroarylamino)(4-(pyridin-2-yl)phenyl)methylphosphonates.

    PubMed

    Prasad, Sthanikam Siva; Kumar, Krishnammagari Suresh; Jayaprakash, Soora Harinath; Krishna, Balam Satheesh; Sundar, Chereddy Syama; Rao, Pasupuleti Visweswara; Babu, Tirumalasetty Munichandra; Rajendra, Wudayagiri; Reddy, Cirandur Suresh

    2013-05-01

    A series of new diethyl(alkyl/aryl/heteroarylamino)(4-(pyridine-2-yl)phenyl)methylphosphonates (4a-t) were synthesized via three-component Kabachnik-Field's reaction of 4-(pyridin-2-yl)benzaldehyde, diethylphosphite and various primary amines, catalyzed by cupric acetate monohydrate [Cu(OAc)(2) ∙ H(2)O] under solvent-free and microwave irradiation conditions. Their computational docking analysis supported them as good therapeutic agents to the breast cancer aromatase enzyme and ascertained 4a, 4h, 4m, 4n, and 4t as potential molecules with good binding affinities varying from -9.0 to -9.6 kcal/mol and containing the 4-(pyridine-2-yl)phenyl moiety as a pharmacophore. Their in vitro screening performed for the anti-cell proliferation activity against MBC-MCF7 cells by MTT and Trypan blue assays confirmed 4m, 4n, and 4q as promising compounds to sustain a low percentage of cell viability at 20 µg/mL concentration. These compounds were also evaluated for their antioxidant activity by the DPPH method and the results established that compounds 4m, 4n, and 4q show around 10% higher activity than the standard antioxidant ascorbic acid.

  3. Design, Synthesis, and Structure-Activity Relationship, Molecular Modeling, and NMR Studies of a Series of a Phenyl Alkyl Ketones as Highly Potent and Selective Phosphodiesterase-4 Inhibitors

    SciTech Connect

    Zheng, S.; Kaur, G; Wang, H; Li, M; MacNaughtan, M; Yang, X; Reid, S; Prestegard, J; Wang, B; et. al.

    2008-01-01

    Phosphodiesterase 4 catalyzes the hydrolysis of cyclic AMP and is a target for the development of anti-inflammatory agents. We have designed and synthesized a series of phenyl alkyl ketones as PDE4 inhibitors. Among them, 13 compounds were identified as having submicromolar IC{sub 50} values. The most potent compounds have IC50 values of in the mid- to low-nanomolar range. Compound 5v also showed preference for PDE4 with selectivity of >2000-fold over PDE7, PDE9, PDE2, and PDE5. Docking of 5v, 5zf, and 5za into the binding pocket of the PDE4 catalytic domain revealed a similar binding profile to PDE4 with rolipram except that the fluorine atoms of the difluoromethyl groups of 5v, 5za, and 5zf are within a reasonable range for hydrogen bond formation with the amide hydrogen of Thr 333 and the long alkyl chain bears additional van der Waals interactions with His 160, Asp 318, and Tyr 159.

  4. Design, Synthesis, and Structure–Activity Relationship, Molecular Modeling, and NMR Studies of a Series of Phenyl Alkyl Ketones as Highly Potent and Selective Phosphodiesterase-4 Inhibitors

    PubMed Central

    Zheng, Shilong; Kaur, Gurpreet; Wang, Huanchen; Li, Minyong; Macnaughtan, Megan; Yang, Xiaochuan; Reid, Suazette; Prestegard, James; Wang, Binghe; Ke, Hengming

    2010-01-01

    Phosphodiesterase 4 catalyzes the hydrolysis of cyclic AMP and is a target for the development of anti-inflammatory agents. We have designed and synthesized a series of phenyl alkyl ketones as PDE4 inhibitors. Among them, 13 compounds were identified as having submicromolar IC50 values. The most potent compounds have IC50 values of in the mid- to low-nanomolar range. Compound 5v also showed preference for PDE4 with selectivity of >2000-fold over PDE7, PDE9, PDE2, and PDE5. Docking of 5v, 5zf, and 5za into the binding pocket of the PDE4 catalytic domain revealed a similar binding profile to PDE4 with rolipram except that the fluorine atoms of the difluoromethyl groups of 5v, 5za, and 5zf are within a reasonable range for hydrogen bond formation with the amide hydrogen of Thr 333 and the long alkyl chain bears additional van der Waals interactions with His 160, Asp 318, and Tyr 159. PMID:19049349

  5. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C88-10-branched alkyl) derivs.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C88...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  6. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C8...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  7. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C8...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  8. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C88-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C88...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  9. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C8...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  10. Thermal Studies of Zn(II), Cd(II) and Hg(II) Complexes of Some N-Alkyl-N-Phenyl-Dithiocarbamates

    PubMed Central

    Onwudiwe, Damian C.; Ajibade, Peter A.

    2012-01-01

    The thermal decomposition of Zn(II), Cd(II) and Hg(II) complexes of N-ethyl-N-phenyl and N-butyl-N-phenyl dithiocarbamates have been studied using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The products of the decomposition, at two different temperatures, were further characterized by scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDX). The results show that while the zinc and cadmium complexes undergo decomposition to form metal sulphides, and further undergo oxidation forming metal oxides as final products, the mercury complexes gave unstable volatiles as the final product. PMID:22949811

  11. The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker.

    PubMed

    Marvania, Bhavin; Kakadiya, Rajesh; Christian, Wilson; Chen, Tai-Lin; Wu, Ming-Hsi; Suman, Sharda; Tala, Kiran; Lee, Te-Chang; Shah, Anamik; Su, Tsann-Long

    2014-08-18

    We synthesized a series of phenyl N-mustard-4-anilinoquinoline conjugates to study their antitumorigenic effects. These agents were prepared by the condensation of 4-[N,N-bis(2-chloroethyl)amino]phenyl isocyanate with 6-amino-4-methylamino or 4-anilinoquinolines. The structure-activity relationship (SAR) studies revealed that the C2-methylquinoline derivatives (18a-o) were generally more cytotoxic than the C2-phenylquinoline conjugates (23a-d) in inhibiting the cell growth of various human tumor cell lines in vitro. However, the methylamino or aniline substituents at C4 of quinoline did not influence the cytotoxic effects. The title conjugates were capable of inducing DNA cross-linking and promoting cell-cycle arrest at the G2/M phase. This study demonstrates that phenyl N-mustard-4-anilinoquinoline conjugates are generally more potent than phenyl N-mustard-4-anilinoquinazoline conjugates against the cell growth of various tumor cell-lines.

  12. Comparative analysis of the influence of bulky β-alkyl substituents on fluorescent properties of some series of spatially distorted meso-phenyl substituted porphyrins

    NASA Astrophysics Data System (ADS)

    Sagun, E. I.; Zenkevich, E. I.

    2013-11-01

    We present results of our systematic investigation and comparative analysis of the spectral-kinetic properties of absorption and fluorescence of two series of related planar porphyrins in liquid media at 293 K, in which deviations from the planarity are caused by contact steric interactions of eight peripheral β-pyrrole methyl (-CH3) or ethyl (-C2H5) groups with a successively increasing number (from one to four) and varying position of meso-phenyl (Ph) substituents in the porphyrin macrocycle. It is substantiated that considerable differences between the spectral-kinetic properties of absorption and fluorescence of the octaethyl- and octamethylporphyrin molecules, which have the same number of meso-phenyl substituents, are caused by fundamentally different roles played by β-ethyl and β-methyl groups, which differ in volume and which determine differences in the character of steric interactions and the efficiency of the dynamic relaxation of the tetrapyrrole macrocycle. It is revealed that there is a difference between calculated f theor and experimentally determined f exp values of the fluorescence probability, which is caused by conformational rearrangements of spatially distorted porphyrin macrocycles in the S 1 excited state, which reduce the oscillator strength and lower the energy of the long-wavelength transition S 0 → S 1. It is found that the chemical nature, the size, and the number of bulky -CH3 or -C2H5 β-pyrrole groups affect weakly rate constants of fluorescence quenching by molecular oxygen and do not create noticeable steric hindrances for contact interactions of the oxygen molecule with the π-conjugated system of the tetrapyrrole macrocycle.

  13. Synthesis of cycloalkyl substituted purine nucleosides via a metal-free radical route.

    PubMed

    Wang, Dong-Chao; Xia, Ran; Xie, Ming-Sheng; Qu, Gui-Rong; Guo, Hai-Ming

    2016-05-04

    An efficient route to synthesize cycloalkyl substituted purine nucleosides was developed. This metal-free C-H activation was accomplished by a tBuOOtBu initiated radical reaction. By adjusting the amount of tBuOOtBu and reaction time, the selective synthesis of C6-monocycloalkyl or C6,C8-dicycloalkyl substituted purine nucleosides could be realized. Furthermore, uracil and related nucleosides were also suitable substrates, giving the C5-cyclohexyl substituted uracil derivatives in good yields with excellent regioselectivities.

  14. Thermochemical properties and bond dissociation energies of C3-C5 cycloalkyl hydroperoxides and peroxy radicals: cycloalkyl radical + (3)O2 reaction thermochemistry.

    PubMed

    Auzmendi-Murua, Itsaso; Bozzelli, Joseph W

    2012-07-19

    Cyclic aliphatic hydrocarbons are major components in modern fuels; they can be present in the reactants, and they can be formed during the gas-phase oxidation processes. In combustion and thermal oxidation processes, these cyclics will form radicals that react with (3)O(2) to form peroxy radicals. In this study, density functional theory and higher level ab initio calculations are used to calculate thermochemical properties and bond dissociation energies of 3-5-membered cycloalkanes, corresponding hydroperoxides, hydroperoxycycloalkyl radicals, and cycloalkyl radicals that occur in these reaction systems. Geometries, vibration frequencies, and thermochemical properties, ΔH(f 298)°, are calculated with the B3LYP/6-31 g(d,p), B3LYP/6-31 g(2d,2p), composite CBS-QB3, and G3MP2B3 methods. Standard enthalpies of formation at 298 K are evaluated using isodesmic reaction schemes with several work reactions for each species. Group additivity contributions are developed, and application of group additivity with comparison to calculated values is illustrated. Entropy and heat capacities, S°(T) and C(p)°(T) (5 K ≤ T ≤ 5000), are determined using geometric parameters and frequencies from the B3LYP/6-31 g(d,p) calculations.

  15. Are Mechanistic and Statistical QSAR Approaches Really Different? MLR Studies on 158 Cycloalkyl-Pyranones.

    PubMed

    Bhhatarai, Barun; Garg, Rajni; Gramatica, Paola

    2010-07-12

    Two parallel approaches for quantitative structure-activity relationships (QSAR) are predominant in literature, one guided by mechanistic methods (including read-across) and another by the use of statistical methods. To bridge the gap between these two approaches and to verify their main differences, a comparative study of mechanistically relevant and statistically relevant QSAR models, developed on a case study of 158 cycloalkyl-pyranones, biologically active on inhibition (Ki ) of HIV protease, was performed. Firstly, Multiple Linear Regression (MLR) based models were developed starting from a limited amount of molecular descriptors which were widely proven to have mechanistic interpretation. Then robust and predictive MLR models were developed on the same set using two different statistical approaches unbiased of input descriptors. Development of models based on Statistical I method was guided by stepwise addition of descriptors while Genetic Algorithm based selection of descriptors was used for the Statistical II. Internal validation, the standard error of the estimate, and Fisher's significance test were performed for both the statistical models. In addition, external validation was performed for Statistical II model, and Applicability Domain was verified as normally practiced in this approach. The relationships between the activity and the important descriptors selected in all the models were analyzed and compared. It is concluded that, despite the different type and number of input descriptors, and the applied descriptor selection tools or the algorithms used for developing the final model, the mechanistical and statistical approach are comparable to each other in terms of quality and also for mechanistic interpretability of modelling descriptors. Agreement can be observed between these two approaches and the better result could be a consensus prediction from both the models.

  16. 40 CFR 721.9530 - Bis(2,2,6,6-tetra-methyl-piper-idinyl) ester of cycloalkyl spir-o-ke-tal.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...) ester of cycloalkyl spir-o-ke-tal. 721.9530 Section 721.9530 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.9530 Bis(2,2,6,6-tetra-methyl-piper-idinyl) ester...) The chemical substance identified generically as bis(2,2,6,6-tetramethyl pi-per-idin-yl) ester of...

  17. Theoretical kinetic study of thermal unimolecular decomposition of cyclic alkyl radicals.

    PubMed

    Sirjean, B; Glaude, P A; Ruiz-Lopèz, M F; Fournet, R

    2008-11-20

    Whereas many studies have been reported on the reactions of aliphatic hydrocarbons, the chemistry of cyclic hydrocarbons has not been explored extensively. In the present work, a theoretical study of the gas-phase unimolecular decomposition of cyclic alkyl radicals was performed by means of quantum chemical calculations at the CBS-QB3 level of theory. Energy barriers and high-pressure-limit rate constants were calculated systematically. Thermochemical data were obtained from isodesmic reactions, and the contribution of hindered rotors was taken into account. Classical transition state theory was used to calculate rate constants. The effect of tunneling was taken into account in the case of CH bond breaking. Three-parameter Arrhenius expressions were derived in the temperature range of 500-2000 K at atmospheric pressure, and the CC and CH bond breaking reactions were studied for cyclic alkyl radicals with a ring size ranging from three to seven carbon atoms, with and without a lateral alkyl chain. For the ring-opening reactions, the results clearly show an increase of the activation energy as the pi bond is being formed in the ring (endo ring opening) in contrast to the cases in which the pi bond is formed on the side chain (exo ring opening). These results are supported by analyses of the electronic charge density that were performed with Atoms in Molecules (AIM) theory. For all cycloalkyl radicals considered, CH bond breaking exhibits larger activation energies than CC bond breaking, except for cyclopentyl for which the ring-opening and H-loss reactions are competitive over the range of temperatures studied. The theoretical results compare rather well with the experimental data available in the literature. Evans-Polanyi correlations for CC and CH beta-scissions in alkyl and cycloalkyl free radicals were derived. The results highlight two different types of behavior depending on the strain energy in the reactant.

  18. Fragrance material review on ethyl phenyl carbinyl acetate.

    PubMed

    McGinty, D; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of ethyl phenyl carbinyl acetate when used as a fragrance ingredient is presented. Ethyl phenyl carbinyl acetate is a member of the fragrance structural group Aryl Alkyl Alcohol Simple Acid Esters (AAASAE). The AAASAE fragrance ingredients are prepared by reacting an aryl alkyl alcohol with a simple carboxylic acid (a chain of 1-4 carbons) to generate formate, acetate, propionate, butyrate, isobutyrate and carbonate esters. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for ethyl phenyl carbinyl acetate were evaluated, then summarized, and includes: physical properties; acute toxicity; skin irritation; and skin sensitization data. A safety assessment of the entire AAASAE will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all AAASAE in fragrances.

  19. Photoreactivity of. cap alpha. -fluorinated phenyl alkyl ketones

    SciTech Connect

    Wagner, P.J.; Thomas, M.J.; Puchalski, A.E.

    1986-11-26

    The photoreactivities of the mono-, di-, and tri-..cap alpha..-fluorinated acetophenones have been compared to that of acetophenone itself. All four ketones have similar triplet excitation energies; the three fluorinated ketones have reduction potentials 0.5-0.7 eV lower than that of acetophenone. Triplet reactivity toward alkylbenzenes keeps increasing with fluorine substitution, since the rate-determining step becomes charge-transfer complexation as the ketone reduction potential decreases. The primary/tertiary C-H selectivity toward p-cymene increases with the number of fluorines. Triplet reactivity toward cyclopentane also is increased by fluorination but peaks at two fluorines, since the lowest triplet switches from n,..pi..* to ..pi..,..pi..* with two or three fluorines and ..pi..,..pi..* triplets are unreactive in simple hydrogen atom abstraction. In contrast, ..cap alpha..-fluorination of valerophenone does not significantly increase the rate of triplet ..gamma..-hydrogen abstraction. The inductive effect on reactivity apparently is offset by a conformational effect. The ..cap alpha..-fluorinated phenones give predominantly cyclobutanols instead of Norrish type II elimination. ..cap alpha..-Fluoroacetophenone forms predominantly acetophenone and HF when irradiated with 2-propanol, in what appears to be a short chain process involving electron transfer to ketone followed by fluoride ion loss. Finally, the radical coupling products in these reactions are formed in varying yields, depending on solvent and additives.

  20. Enantiomerically Pure Acetals in Organic Synthesis: Resolutions and Diastereoselective Alkylations of Alpha-Hydroxy Esters

    DTIC Science & Technology

    1990-01-01

    properties and the potential exists for their separation. A survey of the alcohols (Scheme 3) (-)- menthol 1, (+)- isomenthol Z, (-)-borneol 3...close to the glyoxylate. Another method beginning with 8-phenylmenthol was developed by Pearson19. Pearson first oxidized 8-phenyl- menthol to the...CONDENSATION Another method of alkylating menthol glycolate esters was 41 developed by Boireau22 . Alkylation of the (-)-menthyl ester of

  1. Antihydrophobic cosolvent effects for alkylation reactions in water solution, particularly oxygen versus carbon alkylations of phenoxide ions.

    PubMed

    Breslow, Ronald; Groves, Kevin; Mayer, M Uljana

    2002-04-10

    Antihydrophobic cosolvents such as ethanol increase the solubility of hydrophobic molecules in water, and they also affect the rates of reactions involving hydrophobic surfaces. In simple reactions of hydrocarbons, such as the Diels-Alder dimerization of 1,3-cyclopentadiene, the rate and solubility data directly reflect the geometry of the transition state, in which some hydrophobic surface becomes hidden. In reactions involving polar groups, such as alkylations of phenoxide ions or S(N)1 ionizations of alkyl halides, cosolvents in water can have other effects as well. However, solvation of hydrophobic surfaces is still important. By the use of structure-reactivity relationships, and comparing the effects of ethanol and DMSO as solvents, it has been possible to sort out these effects. The conclusions are reinforced by an ab initio computer model for hydrophobic solvation. The result is a sensible transition state for phenoxide ion as a nucleophile, using its oxygen n electrons to avoid loss of conjugation. The geometry of alkylation of aniline is very different, involving packing (stacking) of the aniline ring onto the phenyl ring of a benzyl group in the benzylation reaction. The alkylation of phenoxide ions by benzylic chlorides can occur both at the phenoxide oxygen and on ortho and para positions of the ring. Carbon alkylation occurs in water, but not in nonpolar organic solvents, and it is observed only when the phenoxide has at least one methyl substituent ortho, meta, or para. The effects of phenol substituents and of antihydrophobic cosolvents on the rates of the competing alkylation processes indicate that in water the carbon alkylation involves a transition state with hydrophobic packing of the benzyl group onto the phenol ring. The results also support our conclusion that oxygen alkylation uses the n electrons of the phenoxide oxygen as the nucleophile and does not have hydrophobic overlap in the transition state. The mechanisms and explanations for

  2. 4-Alkyl radical extrusion in the cytochrome P-450-catalyzed oxidation of 4-alkyl-1,4-dihydropyridines

    SciTech Connect

    Lee, J.S.; Jacobsen, N.E.; Ortiz de Montellano, P.R. )

    1988-10-04

    Rat liver microsomal cytochrome P-450 oxidizes the 4-methyl, 4-ethyl (DDEP), and 4-isopropyl derivatives of 3,5-bis(carbethoxy)-2,6-dimethyl-1,4,-dihydropyridine to mixtures of the corresponding 4-alkyl and 4-dealkyl pyridines. A fraction of the total microsomal enzyme is destroyed in the process. The 4-dealkyl to 4-alkyl pyridine metabolite ratio, the extent of cytochrome P-450 destruction, and the rate of spin-trapped radical accumulation are correlated in a linear inverse manner with the homolytic or heterolytic bond energies of the 4-alkyl groups of the 4-alkyl-1,4-dihydropyridines. No isotope effects are observed on the pyridine matabolite ratio, the destruction of cytochrome P-450, or the formation of ethyl radicals when (4-{sup 2}H)DDEP is used instead of DDEP. N-Methyl- and N-ethyl-DDEP undergo N-dealkylation rather than aromatization but N-phenyl-DDEP is oxidized to a mixture of the 4-ethyl and 4-deethyl N-phenylpyridinium metabolites. In contrast to the absence of an isotope effect in the oxidation of DDEP, the 4-deethyl to 4-ethyl N-phenylpyridinium metabolite ratio increases 6-fold when N-phenyl(4-{sup 2}H)DDEP is used. The results support the hypothesis that cytochrome P-450 catalyzes the oxidation of dihydropyridines to radical cations and show that the radical cations decay to nonradical products by multiple, substituent-dependent, mechanisms.

  3. Reaction of 1-chloro-1-methylcyclohexane with phenyl- and benzyl-trimethylsilanes in the presence of aluminum chloride

    SciTech Connect

    Bolestova, G.I.; Parnes, Z.N.; Vol'pin, M.E.

    1988-10-20

    In the reaction of 1-chloro-1-methylcyclohexane with phenyltrimethylsilane and benzyltrimethylsilane in the presence of aluminum chloride the chlorine atom is substituted by a phenyl or benzyl group with the formation of 1-methyl-1-phenyl- and 1-methyl-1-benzylcyclohexane, respectively. In the case of benzyltrimethylsilane the products from alkylation of the benzene ring of the benzyltrimethylsilane by the 1-methylcyclohexyl carbocation in the Friedel-Crafts reaction are formed in addition to 1-methyl-1-benzylcyclohexane.

  4. Synthesis Of Alkyl Hydroperoxides Via Alkylation Of gem-Dihydroperoxides

    PubMed Central

    Kyasa, ShivaKumar; Puffer, Benjamin W.

    2013-01-01

    Two-fold alkylation of 1,1-dihydroperoxides, followed by hydrolysis of the resulting bisperoxyacetals, provides a convenient method for synthesis of primary and secondary alkyl hydroperoxides. PMID:23469994

  5. One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

    PubMed Central

    Peshkov, Roman Yu; Chunyan, Wang; Tretyakov, Evgeny V; Shteingarts, Vitalij D

    2016-01-01

    Summary A convenient one-pot approach to alkylcyanobiaryls is described. The method is based on biaryl cross-coupling between the sodium salt of the terephthalonitrile dianion and a neutral aromatic nitrile in liquid ammonia, and successive alkylation of the long-lived anionic intermediate with alkyl bromides. The reaction is compatible with benzonitriles that contain methyl, methoxy and phenyl groups, fluorine atoms, and a 1-cyanonaphthalene residue. The variety of ω-substituted alkyl bromides, including an extra bromine atom, a double bond, cyano and ester groups, as well as a 1,3-dioxane fragment are suitable as alkylation reagents. PMID:27559409

  6. Enantioselective synthesis of 4-substituted tetrahydroisoquinolines via palladium-catalyzed intramolecular Friedel-Crafts type allylic alkylation of phenols.

    PubMed

    Zhao, Zheng-Le; Xu, Qing-Long; Gu, Qing; Wu, Xin-Yan; You, Shu-Li

    2015-03-14

    Palladium-catalyzed asymmetric intramolecular Friedel-Crafts type allylic alkylation reaction of phenols was developed under mild conditions. In the presence of Pd2(dba)3 with (1R,2R)-DACH-phenyl Trost ligand (L2) in toluene at 50 °C, the reaction provides various C4 substituted tetrahydroisoquinolines with moderate to excellent yields, regioselectivity and enantioselectivity.

  7. Method of making alkyl esters

    DOEpatents

    Elliott, Brian

    2010-09-14

    Methods of making alkyl esters are described herein. The methods are capable of using raw, unprocessed, low-cost feedstocks and waste grease. Generally, the method involves converting a glyceride source to a fatty acid composition and esterifying the fatty acid composition to make alkyl esters. In an embodiment, a method of making alkyl esters comprises providing a glyceride source. The method further comprises converting the glyceride source to a fatty acid composition comprising free fatty acids and less than about 1% glyceride by mass. Moreover, the method comprises esterifying the fatty acid composition in the presence of a solid acid catalyst at a temperature ranging firm about 70.degree. C. to about 120.degree. C. to produce alkyl esters, such that at least 85% of the free fatty acids are converted to alkyl esters. The method also incorporates the use of packed bed reactors for glyceride conversion and/or fatty acid esterification to make alkyl esters.

  8. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  9. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  10. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  11. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  12. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  13. Polyimides with pendant alkyl groups

    NASA Technical Reports Server (NTRS)

    Jensen, B. J.; Young, P. R.

    1982-01-01

    The effect on selected polyimide properties when pendant alkyl groups were attached to the polymer backbone was investigated. A series of polymers were prepared using benzophenone tetracarboxylic acid dianhydride (BTDA) and seven different p-alkyl-m,p'-diaminobenzophenone monomers. The alkyl groups varied in length from C(1) (methyl) to C(9) (nonyl). The polyimide prepared from BTDA and m,p'-diaminobenzophenone was included as a control. All polymers were characterized by various chromatographic, spectroscopic, thermal, and mechanical techniques. Increasing the length of the pendant alkyl group resulted in a systematic decrease in glass transition temperature (Tg) for vacuum cured films. A 70 C decrease in Tg to 193 C was observed for the nonyl polymer compared to the Tg for the control. A corresponding systematic increase in Tg indicative of crosslinking, was observed for air cured films. Thermogravimetric analysis revealed a slight sacrifice in thermal stability with increasing alkyl length. No improvement in film toughness was observed.

  14. Syntheses and analytical characterizations of N-alkyl-arylcyclohexylamines.

    PubMed

    Wallach, Jason; Colestock, Tristan; Cicali, Brian; Elliott, Simon P; Kavanagh, Pierce V; Adejare, Adeboye; Dempster, Nicola M; Brandt, Simon D

    2016-08-01

    The rise in new psychoactive substances that are available as 'research chemicals' (RCs) remains a significant forensic and legislative challenge. A number of arylcyclohexylamines have attracted attention as RCs and continue to be encountered, including 3-MeO-PCP, 3-MeO-PCE and 3-MeO-PCPr. These compounds are commonly perceived as ketamine-like dissociative substances and are believed to act predominantly via antagonism of the N-methyl-D-aspartate (NMDA) receptor. To aid in the identification of newly emerging substances of abuse, the current studies were performed. The syntheses of fifteen N-alkyl-arylcyclohexylamines are described. Analytical characterizations were performed via gas chromatography and high performance liquid chromatography coupled to multiple forms of mass spectrometry as well as nuclear magnetic resonance spectroscopy, ultraviolet diode array detection and infrared spectroscopy. The series consisted of the N-alkyl derivatives (N-methyl, N-ethyl, N-propyl) of phenyl-substituted and isomeric 2-, 3- and 4-methoxy phenylcyclohexylamines, as well as the N-alkyl derivatives obtained from 3-methylphenyl and 2-thienyl moieties. In addition to the presentation of a range of previously unreported data, it was also found that positional isomers of aryl methoxyl-substituted arylcyclohexylamines were readily distinguishable under a variety of analytical conditions. Copyright © 2015 John Wiley & Sons, Ltd.

  15. 1-Phenyl­isatin

    PubMed Central

    Shukla, Deepak; Rajeswaran, Manju

    2011-01-01

    In the title compound, C14H9NO2, the phenyl ring makes a dihedral angle of 50.59 (5)° with the mean plane of the isatin fragment. In the crystal, mol­ecules are linked through weak inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits two slipped π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.968 (3) Å, inter­planar distance = 3.484 (3) Å and slippage = 1.899 (3) Å], and between the phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.968 (3) Å, inter­planar distance = 3.638 (3) Å and slippage = 1.584 (3) Å]. PMID:22091062

  16. Mild Catalytic methods for Alkyl-Alkyl Bond Formation

    SciTech Connect

    Vicic, David A

    2009-08-10

    Overview of Research Goals and Accomplishments for the Period 07/01/06 – 06/30/07: Our overall research goal is to transform the rapidly emerging synthetic chemistry involving alkyl-alkyl cross-couplings into more of a mechanism-based field so that that new, rationally-designed catalysts can be performed under energy efficient conditions. Our specific objectives for the previous year were 1) to obtain a proper electronic description of an active catalyst for alkyl-alkyl cross-coupling reactions and 2) to determine the effect of ligand structure on the rate, scope, selectivity, and functional group compatibility of C(sp3)-C(sp3) cross-coupling catalysis. We have completed both of these initial objectives and established a firm base for further studies. The specific significant achievements of the current grant period include: 1) we have performed magnetic and computational studies on (terpyridine)NiMe, an active catalyst for alkyl-alkyl cross couplings, and have discovered that the unpaired electron resides heavily on the terpyridine ligand and that the proper electronic description of this nickel complex is a Ni(II)-methyl cation bound to a reduced terpyridine ligand; 2) we have for the first time shown that alkyl halide reduction by terpyridyl nickel catalysts is substantially ligand based; 3) we have shown by isotopic labeling studies that the active catalyst (terpyridine)NiMe is not produced via a mechanism that involves the formation of methyl radicals when (TMEDA)NiMe2 is used as the catalyst precursor; 4) we have performed an extensive ligand survey for the alkyl-alkyl cross-coupling reactions and have found that electronic factors only moderately influence reactivity in the terpyridine-based catalysis and that the most dramatic effects arise from steric and solubility factors; 5) we have found that the use of bis(dialkylphosphino)methanes as ligands for nickel does not produce active catalysts for cross-coupling but rather leads to bridging hydride

  17. Phenylated Polyimides With Greater Solubility

    NASA Technical Reports Server (NTRS)

    Harris, Frank W.

    1991-01-01

    In experiments, 3,6-diphenylpyromellitic dianhydride monomer prepared and polymerized with several different diamines. Polyimides with pendent phenyl groups along polymer backbones considerably more soluble than PMDA-based materials. Increased solubility eases processing, providing increased potential use in variety of applications. Because most polymers soluble in organic solvents, usable in microelectronics applications. Excellent thermal stabilities and high transition temperatures make them ideally suited. Many polymers extremely rigid and useful as reinforcing polymers in molecular composites. More flexible compositions useful as matrix resins in carbon-reinforced composites.

  18. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  19. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  20. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  1. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  2. Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter.

    PubMed

    Froimowitz, Mark; Gu, Yonghong; Dakin, Les A; Nagafuji, Pamela M; Kelley, Charles J; Parrish, Damon; Deschamps, Jeffrey R; Janowsky, Aaron

    2007-01-25

    Methylphenidate analogues, in which the carbomethoxy has been replaced by an alkyl group and with different phenyl substituents, have been synthesized and tested in monoamine transporter assays. As predicted from a pharmacophore model, most of the RR/SS diastereomers showed high potency as dopamine reuptake inhibitors. Analogues with a 4-chlorophenyl group and an unbranched initial alkyl atom had consistently enhanced selectivity for the dopamine transporter. The most potent compounds were those with a three- or four-carbon chain. The "inactive" RS/SR diastereomers showed substantial activity when the phenyl substituent was 3,4-dichloro. On a locomotor assay, one compound was found to have a slow onset and a long duration of action. The activity of these compounds provides additional evidence for a conformational/superposition model of methylphenidate with cocaine-like structures. A ketone analogue, obtained by hydrogenating a previously described vinylogous amide, had activity similar to that of methylphenidate.

  3. Outlook for the U. S. alkylation industry

    SciTech Connect

    Felten, J.R.; Bradshaw, T.; McCarthy, K. )

    1994-01-01

    Alkylation has long been recognized in the refining industry as one of the best options to convert refinery olefins into valuable, clean, high octane blending components. In fact, refinery alkylation is a preferred source of blending stocks for reformulated gasoline. However, the hydrofluoric acid (HF) alkylation process and, to a lesser extent, the sulfuric acid (SA) process have come under increasing pressure in the US due to safety and environmental concerns. This paper examines the current outlook for the US alkylation industry including: key trends and driving forces in the industry, the impact of environmental issues on both HF and SA alkylation, US alkylation supply/demand forecast including the outlook for oxygenates, how US refines will respond to the increased demand and restricted supply for alkylates, and the outlook for new solid acid alkylation (SAC) technology.

  4. Total synthesis of alkyl citrate natural products.

    PubMed

    Rizzacasa, Mark A; Sturgess, Dayna

    2014-03-07

    This review highlights the synthesis of members of the alkyl citrate family of natural products. The focus is on the stereoselective construction of the alkyl citrate moiety common to these compounds.

  5. Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.

    PubMed

    Jeffrey, Jenna L; Sarpong, Richmond

    2012-11-02

    Direct C(6) alkylation of pyridyl alcohols can be achieved following an initial deprotonation of the hydroxy group. This transformation, which is believed to occur by a Chichibabin-type alkylation, avoids lateral deprotonation prior to pyridine ring alkylation and gives increased regioselectivity for C(6) over C(4) alkylation.

  6. Refiners discuss HF alkylation process and issues

    SciTech Connect

    Not Available

    1992-04-06

    Safety and oxygenate operations made HF alkylation a hot topic of discussion at the most recent National Petroleum Refiners Association annual question and answer session on refining and petrochemical technology. This paper provides answers to a variety of questions regarding the mechanical, process, and safety aspects of the HF alkylation process. Among the issues discussed were mitigation techniques, removal of oxygenates from alkylation unit feed, and amylene alkylation.

  7. 40 CFR 721.9892 - Alkylated urea.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkylated urea. 721.9892 Section 721... Alkylated urea. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an alkylated urea (PMN P-93-1649) is subject to reporting under...

  8. Models for cytochrome P450 prosthetic heme alkylation. Reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) chloride

    SciTech Connect

    Komives, E.A.; Tew, D.; Olmstead, M.M.; Ortiz de Montellano, P.R.

    1988-09-07

    The reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) yields (N-(2-phenyl-2-oxoethyl)tetraphenylporphyrinato)iron(II) chloride. The structure of this product has been established by spectroscopic methods and by x-ray crystallography. The crystal structure shows that the first carbon of the N-alkyl group is 2.94 /angstrom/ from the iron atom and that the oxygen of the N-alkyl group points away from the iron. No evidence is seen for the Fe-C-N product expected from insertion of the diazo carbon into the metalloporphyrin iron-nitrogen bond or for intermediates in which the oxygen of the N-(2-phenyl-2-oxoethyl) group is coordinated to the iron. These results suggest it is unlikely that carbene-insertion or oxygen-coordinated intermediates will be detected during the N-alkylation of cytochrome P450 by diazo ketones. The results also rationalize the failure to detect iron-chelated enol species during N-alkylation of the prosthetic group of cytochrome P450 by catalytically activated phenylacetylene. 43 references, 5 figures, 4 tables.

  9. 40 CFR 721.4472 - Phenyl, alkyl, hydroxyalkyl substituted imidazole (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant... test guideline) followed by a (90-day subchronic inhalation study in rats (40 CFR 799.9346). A...

  10. 40 CFR 721.4472 - Phenyl, alkyl, hydroxyalkyl substituted imidazole (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant... test guideline) followed by a (90-day subchronic inhalation study in rats (40 CFR 799.9346). A...

  11. 40 CFR 721.4472 - Phenyl, alkyl, hydroxyalkyl substituted imidazole (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant... test guideline) followed by a (90-day subchronic inhalation study in rats (40 CFR 799.9346). A...

  12. 40 CFR 721.4472 - Phenyl, alkyl, hydroxyalkyl substituted imidazole (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant... test guideline) followed by a (90-day subchronic inhalation study in rats (40 CFR 799.9346). A...

  13. 40 CFR 721.4472 - Phenyl, alkyl, hydroxyalkyl substituted imidazole (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant... test guideline) followed by a (90-day subchronic inhalation study in rats (40 CFR 799.9346). A...

  14. Methods of making alkyl esters

    DOEpatents

    Elliott, Brian

    2010-08-03

    A method comprising contacting an alcohol, a feed comprising one or more glycerides and equal to or greater than 2 wt % of one or more free fatty acids, and a solid acid catalyst, a nanostructured polymer catalyst, or a sulfated zirconia catalyst in one or more reactors, and recovering from the one or more reactors an effluent comprising equal to or greater than about 75 wt % alkyl ester and equal to or less than about 5 wt % glyceride.

  15. PREPARATION OF ALKYL PYROPHOSPHATE EXTRACTANTS

    DOEpatents

    Levine, C.A.; Skiens, W.E.; Moore, G.R.

    1960-08-01

    A process for providing superior solvent extractants for metal recovery processes is given wherein the extractant comprises an alkyl pyrophosphoric acid ester dissolved in an organic solvent diluent. Finely divided solid P/sub 2/O/ sub 5/ is slurried in an organic solvent-diluent selected from organic solvents such as kerosene, benzene, chlorobenzene, toluene, etc. An alcohol selected from the higher alcohols having 4 to 17 carbon atoms. e.g.. hexanol-1. heptanol-3, octanol-1. 2.6-dimethyl-heptanol-4, and decanol-1, is rapidly added to the P/sub 2/O/sub 5/ slurry in the amount of about 2 moles of alcohol to 1 mole of P/sub 2/ O/sub 5/. The temperature is maintained below about 110 deg C during the course of the P/sub 2/O/sub 5/-alcohol reaction. An alkyl pyrophosphate extractant compound is formed as a consequence of the reaction process. The alkyl pyrophosphate solvent-diluent extractant phase is useful in solvent extraction metal recovery processes.

  16. Testing Consent Order on Dilsodecyl Phenyl Phosphite

    EPA Pesticide Factsheets

    This rule announces that EPA has signed an enforceable Testing Consent Order with three manufacturers of dilsodecyl phenyl phosphite (PDDP CAS No, 25550-98-5), who have agreed to perform certain neurotoxicity tests PDDP.

  17. Iron-Catalyzed Decarboxylative Alkyl Etherification of Vinylarenes with Aliphatic Acids as the Alkyl Source.

    PubMed

    Jian, Wujun; Ge, Liang; Jiao, Yihang; Qian, Bo; Bao, Hongli

    2017-03-20

    Because of the lack of effective alkylating reagents, alkyl etherification of olefins with general alkyl groups has not been previously reported. In this work, a variety of alkyl diacyl peroxides and peresters generated from aliphatic acids have been found to enable the first iron-catalyzed alkyl etherification of olefins with general alkyl groups. Primary, secondary and tertiary aliphatic acids are suitable for this reaction, delivering products with yields up to 97 %. Primary and secondary alcohols react well, affording products in up to 91 % yield.

  18. Novel thiol-based histone deacetylase inhibitors bearing 3-phenyl-1H-pyrazole-5-carboxamide scaffold as surface recognition motif: Design, synthesis and SAR study.

    PubMed

    Wen, Jiachen; Niu, Qun; Liu, Jiang; Bao, Yu; Yang, Jinyu; Luan, Shenglin; Fan, Yinbo; Liu, Dan; Zhao, Linxiang

    2016-01-15

    A series of novel thiol-based histone deacetylase (HDAC) inhibitors bearing 3-phenyl-1H-pyrazole-5-carboxamide scaffold as surface recognition motif was designed, synthesized, and evaluated for their HDAC inhibition activity. Among them, 15j (IC50=0.08μM) was identified as a better inhibitor than Vorinostat (IC50=0.25μM) against total HDACs. In addition, Structure-activity relationships (SAR) analyses indicated that (i) compounds with different substituents on pyrazole N-1 position exhibited superior activities than those on pyrazole N-2 position, (ii) variation of functional groups on N-1'-alkyl chain terminus followed the trends of carboxyl group>hydroxyl group≫alkyl group, and (iii) methylation on pyrazole C-4 position diminished the HDAC inhibition activity. The SAR will guide us to further refine compounds bearing 3-phenyl-1H-pyrazole-5-carboxamide scaffold to achieve better HDAC inhibitors.

  19. Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions.

    PubMed

    Breitenfeld, Jan; Ruiz, Jesus; Wodrich, Matthew D; Hu, Xile

    2013-08-14

    Many nickel-based catalysts have been reported for cross-coupling reactions of nonactivated alkyl halides. The mechanistic understanding of these reactions is still primitive. Here we report a mechanistic study of alkyl-alkyl Kumada coupling catalyzed by a preformed nickel(II) pincer complex ([(N2N)Ni-Cl]). The coupling proceeds through a radical process, involving two nickel centers for the oxidative addition of alkyl halide. The catalysis is second-order in Grignard reagent, first-order in catalyst, and zero-order in alkyl halide. A transient species, [(N2N)Ni-alkyl(2)](alkyl(2)-MgCl), is identified as the key intermediate responsible for the activation of alkyl halide, the formation of which is the turnover-determining step of the catalysis.

  20. Reactions of Tributylstannyl Anioniods with Alkyl Bromides.

    DTIC Science & Technology

    1981-09-28

    g (12 mmol) of cesium tert-butoxide was added to the reaction vessel before the addition of n-butyllithium. Alkylation of Tributylstannyl Anionoids...Dry reaction vessels were purged with argon. The desired alkyl halide (1.0 mmol unless noted) and any desired additive were added to the reaction ...OFFICE OF NAVAL RESEARCH Contract N00014-79-C-0584 Task No. NR 053-714 TECHNICAL REPORT No. 2 Reactions of Tributylstannyl Anionoids with Alkyl

  1. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.3063 Substituted phenyl azo substituted phenyl esters (generic name). Link to an amendment published at 79 FR 34637, June 18, 2014. (a)...

  2. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... alkyl esters (generic name). 721.1875 Section 721.1875 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  3. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... alkyl esters (generic name). 721.1875 Section 721.1875 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  4. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... alkyl esters (generic name). 721.1875 Section 721.1875 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  5. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... alkyl esters (generic name). 721.1875 Section 721.1875 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  6. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... alkyl esters (generic name). 721.1875 Section 721.1875 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to...

  7. Facile, regioselective [4 + 2] cycloaddition involving 1-aryl-4-phenyl-1-azadienes and allenic esters: an efficient route to novel substituted 1-aryl-4-phenyl-1,4-dihydropyridines.

    PubMed

    Ishar, M P; Kumar, K; Kaur, S; Kumar, S; Girdhar, N K; Sachar, S; Marwaha, A; Kapoor, A

    2001-07-12

    [reaction: see text]1-Aryl-4-phenyl-1-azadienes undergo facile, regioselective [4 + 2] cycloaddition to the C2,C3 pi-bond of allenic esters in refluxing benzene, and the formed adducts undergo a 1,3-H shift to afford novel 2-alkyl-1-aryl-3-ethoxycarbonyl-4-phenyl-1,4-dihydropyridines (78-97%). However, when the reaction is carried at room temperature, besides the [4 + 2] addition, the [2 + 2] mode of addition involving C=N of azadiene and C3,C4 pi-bond of allenic esters also intervenes. The resulting N-aryl-2-ethoxy-carbonyl-methylidene-4-styrylazetidines (17-28%) undergo reorganization on silica gel to afford 2-cyclohexen-1-ones.

  8. S-alkylation of soft scorpionates.

    PubMed

    Rajasekharan-Nair, Rajeev; Moore, Dean; Chalmers, Kirsten; Wallace, Dawn; Diamond, Louise M; Darby, Lisa; Armstrong, David R; Reglinski, John; Spicer, Mark D

    2013-02-11

    The alkylation reactions of soft scorpionates are reported. The hydrotris(S-alkyl-methimazolyl)borate dications (alkyl = methyl, allyl, benzyl), which were prepared by the reaction of Tm(Me) anion and primary alkyl halides, have been isolated and structurally characterised. The reaction is, however, not universally successful. DFT analysis of these alkylation reactions (C=S versus B-H alkylation) indicates that the observed outcome is driven by kinetic factors. Extending the study to incorporate alternative imine thiones (mercaptobenzothiazole, bz; thiazoline, tz) led to the structural characterisation of di[aquo-μ-aquohydrotris(mercaptobenzothiazolyl)boratosodium], which contains sodium atoms in the κ(3)-S,S,S coordination mode. Alkylation of Na[Tbz] and Na[tzTtz] leads to decomposition resulting in the formation of the simple S-alkylated heterocycles. The analysis of the species involved in these reactions shows an inherent weakness in the B-N bond in soft scorpionates, which has implications for their use in more advanced chemistry.

  9. Occupational asthma due to alkyl cyanoacrylate

    SciTech Connect

    Nakazawa, T. )

    1990-08-01

    A case of bronchial asthma induced by occupational exposure to alkyl cyanoacrylate, an adhesive, occurred in an assembly operation. Provocative exposure testing induced immediate and delayed asthmatic responses. Alkyl cyanoacrylate seemed to act as an allergen or as an irritant, resulting in the development of asthma.

  10. Redox shuttle additives for lithium-ion batteries

    DOEpatents

    Zhang, Lu; Zhang, Zhengcheng; Amine, Khalil

    2017-03-21

    An electro lye includes a compound of Formula I or IA: where each instance of R.sup.1 is independently H, alkyl, alkoxy, alkenyl, aryl, heteroaryl, or cycloalkyl; each instance of R.sup.2 is independently H, alkyl, alkoxy, alkenyl, aryl, heteroaryl, or cycloalkyl; each instance of R.sup.3 is independently H, alkyl, alkenyl, aryl, or cycloalkyl; each instance of R.sup.4 is independently H, halogen, CN, NO.sub.2, phosphate, alkyl, alkenyl, aryl, heteroaryl, or cycloalkyl; x is 1, 2, 3, 4, or 5; y is 1 or 2; and z is 0, 1, 2, 3, or 4. ##STR00001##

  11. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, L.A. Jr.

    1989-07-18

    Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C[sub 2] to C[sub 10] olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80 C to 500 C, using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms. 1 fig.

  12. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, Jr., Lawrence A.; Arganbright, Robert P.; Hearn, Dennis

    1994-01-01

    Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.

  13. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, L.A. Jr.; Arganbright, R.P.; Hearn, D.

    1993-09-07

    Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C[sub 2] to C[sub 10] olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80 C to 500 C, using as the catalyst a molecular sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene to about the mid point of the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms. 1 figures.

  14. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, L.A. Jr.; Arganbright, R.P.; Hearn, D.

    1993-01-05

    Aromatic compounds are alkylated in a combination reactor/distillation column comprising a vessel suitable for operating between 70 C and 500 C and from 0.5 to 20 atmospheres pressure; an inert distillation packing in the lower one-third of said vessel; solid acidic catalytic material such as zeolites or an acidic cation exchange resin supported in the middle one-third of said vessel; and inert distillation packing in the upper one-third of said vessel. A benzene inlet is located near the upper end of the vessel; an olefin inlet is juxtaposed with said solid acidic catalytic material; a bottoms outlet is positioned near the bottom of said vessel for removing said cumene and ethyl benzene; and an overhead outlet is placed at the top of said vessel for removing any unreacted benzene and olefin.

  15. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, Jr., Lawrence A.

    1989-01-01

    Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.

  16. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, Jr., Lawrence A.; Arganbright, Robert P.; Hearn, Dennis

    1993-01-01

    Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene to about the mid point of the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.

  17. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, Jr., Lawrence A.; Arganbright, Robert P.; Hearn, Dennis

    1993-01-01

    Aromatic compounds are alkylated in a combination reactor/distillation column comprising a vessel suitable for operating between 70.degree. C. and 500.degree. C. and from 0.5 to 20 atmospheres pressure; an inert distillation packing in the lower one-third of said vessel; solid acidic catalytic material such as zeolites or an acidic cation exchange resin supported in the middle one-third of said vessel; and inert distillation packing in the upper one-third of said vessel. A benzene inlet is located near the upper end of the vessel; an olefin inlet is juxtaposed with said solid acidic catalytic material; a bottoms outlet is positioned near the bottom of said vessel for removing said cumene and ethyl benzene; and an overhead outlet is placed at the top of said vessel for removing any unreacted benzene and olefin.

  18. Alkylation of organic aromatic compounds

    DOEpatents

    Smith, L.A. Jr.; Arganbright, R.P.; Hearn, D.

    1994-06-14

    Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C[sub 2] to C[sub 10] olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80 C to 500 C, using as the catalyst a molecular sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms. 1 fig.

  19. Boron-containing organosilane polymers and ceramic materials thereof

    NASA Technical Reports Server (NTRS)

    Riccitiello, Salvatore R. (Inventor); Hsu, Ming-Ta S. (Inventor); Chen, Timothy S. (Inventor)

    1989-01-01

    The present invention relates to a polyorgano borosilane ceramic precursor polymer comprising a plurality of repeating units of the formula: (R(sup 1) single bond B)(sub p) being linked together at B by second units of the formula: single bond (R sup 2) single bond (Si single bond R sup 3) single bond (sub q), where R(sup 1) is a lower alkyl, cycloalkyl, phenyl, or (R(sup 2)R(sup 3) single bond Si single bond B single bond)(sub n) and R(sup 2) and R(sup 3) are each independently selected from hydrogen, lower alkyl, vinyl, cycloalkyl, or aryl, n is an integer between 1 and 100; p is an integer between 1 and 100; and q is an integer between 1 and 100. These materials are prepared by combining an organo borohalide of the formula R(sup 4) single bond B single bond (X sup 1) (sub 2) where R(sup 4) is selected from halogen, lower alkyl, cycloalkyl, or aryl, and an organo halosilane of the formula: R(sup 2)(R sup 3)Si(X sup 2)(sub 2) where R(sup 2) and R (sup 3) are each independently selected from lower alkyl, cycloalkyl, or aryl, and X(sup 1) and X(sup 2) are each independently selected from halogen, in an anhydrous aprotic solvent having a boiling point at ambient pressure of not greater than 160 C with in excess of four equivalents of an alkali metal, heating the reaction mixture and recovering the polyorgano borosilane. These silicon boron polymers are useful to generate high-temperature ceramic materials, such as SiC, SiB4, and B4C, upon thermal degradation above 600 C.

  20. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  1. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  2. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  3. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  4. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  5. 40 CFR 721.536 - Halogenated phenyl alkane.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Halogenated phenyl alkane. 721.536... Substances § 721.536 Halogenated phenyl alkane. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as halogenated phenyl alkane (PMN P-89-867)...

  6. Ultraviolet photodissociation dynamics of the phenyl radical

    SciTech Connect

    Song Yu; Lucas, Michael; Alcaraz, Maria; Zhang Jingsong; Brazier, Christopher

    2012-01-28

    Ultraviolet (UV) photodissociation dynamics of jet-cooled phenyl radicals (C{sub 6}H{sub 5} and C{sub 6}D{sub 5}) are studied in the photolysis wavelength region of 215-268 nm using high-n Rydberg atom time-of-flight and resonance enhanced multiphoton ionization techniques. The phenyl radicals are produced from 193-nm photolysis of chlorobenzene and bromobenzene precursors. The H-atom photofragment yield spectra have a broad peak centered around 235 nm and are in good agreement with the UV absorption spectra of phenyl. The H + C{sub 6}H{sub 4} product translational energy distributions, P(E{sub T})'s, peak near {approx}7 kcal/mol, and the fraction of average translational energy in the total excess energy, , is in the range of 0.20-0.35 from 215 to 268 nm. The H-atom product angular distribution is isotropic. The dissociation rates are in the range of 10{sup 7}-10{sup 8} s{sup -1} with internal energy from 30 to 46 kcal/mol above the threshold of the lowest energy channel H +o-C{sub 6}H{sub 4} (ortho-benzyne), comparable with the rates from the Rice-Ramsperger-Kassel-Marcus theory. The results from the fully deuterated phenyl radical are identical. The dissociation mechanism is consistent with production of H +o-C{sub 6}H{sub 4}, as the main channel from unimolecular decomposition of the ground electronic state phenyl radical following internal conversion of the electronically excited state.

  7. Rotational spectra and conformational structures of 1-phenyl-2-propanol, methamphetamine, and 1-phenyl-2-propanone.

    PubMed

    Tubergen, M J; Lavrich, R J; Plusquellic, D F; Suenram, R D

    2006-12-14

    Microwave spectra have been recorded for 1-phenyl-2-propanol, methamphetamine, and 1-phenyl-2-propanone from 11 to 24 GHz using a Fourier-transform microwave spectrometer. Only one spectrum from a single conformational isomer was observed for each species. The rotational transitions in the spectrum of 1-phenyl-2-propanone were split into separate transitions arising from the A- and E-torsional levels of the methyl rotor. The fit of the E-state transitions to a "high-barrier" internal rotation Hamiltonian determines V3 = 238(1) cm-1 and rotor-axis angles of thetaa = 87.7(5) degrees, thetab = 50.0(5) degrees, and thetac = 40.0(5) degrees. Ab initio optimizations (MP2/6-31G**) and single-point calculations (MP2/6-311++G**) were used to model the structures of 1-phenyl-2-propanol, methamphetamine, and 1-phenyl-2-propanone. The lowest energy conformations of these species were found to be stabilized by weak OH-pi, NH-pi, and CH-pi hydrogen-bonding interactions. Moments of inertia, derived from the model structures, were used to assign the spectra to the lowest energy conformation of each species. A series of MP2/6-31G* partial optimizations along the internal rotation pathway were used to estimate the barrier to methyl rotation to be 355 cm-1 for 1-phenyl-2-propanone.

  8. Regioselectivity of Birch reductive alkylation of biaryls.

    PubMed

    Lebeuf, Raphaël; Robert, Frédéric; Landais, Yannick

    2005-10-13

    [reaction: see text] The regioselectivity of the Birch reductive alkylation of polysubstituted biaryls has been investigated. Results indicate that regioselectivity is affected by the electronic nature of substituents on both aromatic rings. The electron-rich 3,5-dimethoxyphenyl moiety is selectively reduced and then alkylated, while phenols and aniline are not dearomatized under these conditions. Biaryls possessing a phenol moiety are alkylated on the second ring, providing that the acidic proton has been removed prior to the Li/NH3 reduction.

  9. Synthesis, Electrochemical Characterization, and Linear Free Energy Relationship of 1,3-Diphenyl-6-alkyl/arylfulvenes.

    PubMed

    Godman, Nicholas P; Adas, Sonya K; Hellwig, Karl M; Ball, David W; Balaich, Gary J; Iacono, Scott T

    2016-10-21

    A series of 1,3-diphenyl-6-alkyl/arylfulvenes was prepared, and the electrochemical properties were investigated. The addition of phenyl groups about the fulvene raised the reduction potential and helped to stabilize the electrochemically generated radical anion. The addition of various functional groups onto the phenyl ring at the 6-position of 1,3,6-triphenylfulvene results in a linear free energy relationship between reduction potential and the Hammett substituent constant, σ. Further extending the conjugation at the 6-position of 1,3-diphenyl-6-arylfulvenes increases the reversibility of the redox reactions, but does not appear to further stabilize the generated radical anion. This in-depth investigation provides evidence that the compounds studied may have utility in light-harvesting applications.

  10. 21 CFR 176.120 - Alkyl ketene dimers.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Alkyl ketene dimers. 176.120 Section 176.120 Food... Use Only as Components of Paper and Paperboard § 176.120 Alkyl ketene dimers. Alkyl ketene dimers may... section. (a) The alkyl ketene dimers are manufactured by the dehydrohalogenation of the acyl...

  11. 21 CFR 176.120 - Alkyl ketene dimers.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Alkyl ketene dimers. 176.120 Section 176.120 Food... Use Only as Components of Paper and Paperboard § 176.120 Alkyl ketene dimers. Alkyl ketene dimers may... section. (a) The alkyl ketene dimers are manufactured by the dehydrohalogenation of the acyl...

  12. Ruthenium-catalyzed meta/ortho-selective C-H alkylation of azoarenes using alkyl bromides.

    PubMed

    Li, Gang; Ma, Xingxing; Jia, Chunqi; Han, Qingqing; Wang, Ya; Wang, Junjie; Yu, Liuyang; Yang, Suling

    2017-01-19

    meta/ortho-Selective CAr-H (di)alkylation reactions of azoarenes have been achieved via [Ru(p-cymene)Cl2]2 catalyzed ortho-metalation using various types of alkyl bromides. Particularly, dual meta-alkylation of azoarene and reduction offer an attractive strategy for the synthesis of meta-alkylanilines, which are difficult to access via traditional aniline functionalization methods.

  13. N-Alkylation by Hydrogen Autotransfer Reactions.

    PubMed

    Ma, Xiantao; Su, Chenliang; Xu, Qing

    2016-06-01

    Owing to the importance of amine/amide derivatives in all fields of chemistry, and also the green and environmentally benign features of using alcohols as alkylating reagents, the relatively high atom economic dehydrative N-alkylation reactions of amines/amides with alcohols through hydrogen autotransfer processes have received much attention and have developed rapidly in recent decades. Various efficient homogeneous and heterogeneous transition metal catalysts, nano materials, electrochemical methods, biomimetic methods, asymmetric N-alkylation reactions, aerobic oxidative methods, and even certain transition metal-free, catalyst-free, or autocatalyzed methods, have also been developed in recent years. With a brief introduction to the background and developments in this area of research, this chapter focuses mainly on recent progress and technical and conceptual advances contributing to the development of this research in the last decade. In addition to mainstream research on homogeneous and heterogeneous transition metal-catalyzed reactions, possible mechanistic routes for hydrogen transfer and alcohol activation, which are key processes in N-alkylation reactions but seldom discussed in the past, the recent reports on computational mechanistic studies of the N-alkylation reactions, and the newly emerged N-alkylation methods based on novel alcohol activation protocols such as air-promoted reactions and transition metal-free methods, are also reviewed in this chapter. Problems and bottlenecks that remained to be solved in the field, and promising new research that deserves greater future attention and effort, are also reviewed and discussed.

  14. 2-Amino-N′-phenyl­benzohydrazide

    PubMed Central

    Kesternich, Víctor; Gahona, Paulo; Pérez-Fehrmann, Marcia; Brito, Iván; López-Rodríguez, Matías

    2012-01-01

    In the title compound, C13H13N3O, the NNCO unit forms dihedral angles of 35.8 (1) and 84.0 (1)° with the benzene and phenyl rings, respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains parallel to the c axis. Neighbouring chains are linked by weak N—H⋯N hydrogen bonds, forming R 4 4(20) rings, and resulting in the formation of a two-dimensional network lying parallel to (010). The packing also features π–π stacking inter­actions between phenyl rings [centroid–centroid distance = 3.803 (2) Å]. PMID:22719614

  15. S-Phenyl benzothio-ate.

    PubMed

    Belay, Yonas H; Kinfe, Henok H; Muller, Alfred

    2012-10-01

    In the title compound, C(13)H(10)OS, the phenyl rings are inclined to one another by 51.12 (8)°. There is a short C-H⋯S contact in the molecule.In the crystal, molecules are linked via C-H⋯O hydrogen bonds forming chains along the a axis. Molecules are also linked by C-H⋯π and weak π-π interactions [centroid-centroid distance = 3.9543 (10) Å].

  16. Phenyl valerate esterase activity of human butyrylcholinesterase.

    PubMed

    Mangas, Iris; Vilanova, Eugenio; Estévez, Jorge

    2017-03-15

    Phenyl valerate is used for detecting and measuring neuropathy target esterase (NTE) and has been used for discriminating esterases as potential target in hen model of organophosphorus delayed neuropathy. In previous studies we observed that phenyl valerate esterase (PVase) activity of an enzymatic fraction in chicken brain might be due to a butyrylcholinesterase protein (BuChE), and it was suggested that this enzymatic fraction could be related to the potentiation/promotion phenomenon of the organophosphate-induced delayed neuropathy (OPIDN). In this work, PVase activity of purified human butyrylcholinesterase (hBuChE) is demonstrated and confirms the novel observation that a relationship of BuChE with PVase activities is also relevant for humans, as is, therefore the potential role in toxicity for humans. The KM and catalytic constant (kcat) were estimated as 0.52/0.72 µM and 45,900/49,200 min(-1) respectively. Furthermore, this work studies the inhibition by preincubation of PVase and cholinesterase activities of hBuChE with irreversible inhibitors (mipafox, iso-OMPA or PMSF), showing that these inhibitors interact similarly in both activities with similar second-order inhibition constants. Acethylthiocholine and phenyl valerate partly inhibit PVase and cholinesterase activities, respectively. All these observations suggest that both activities occur in the same active center. The interaction with a reversible inhibitor (ethopropazine) showed that the cholinesterase activity was more sensitive than the PVase activity, showing that the sensitivity for this reversible inhibitor is affected by the nature of the substrate. The present work definitively establishes the capacity of BuChE to hydrolyze the carboxylester phenyl valerate using a purified enzyme (hBuChE). Therefore, BuChE should be considered in the research of organophosphorus targets of toxicity related with PVase proteins.

  17. Mechanisms of catalytic cleavage of benzyl phenyl ether in aqueous and apolar phases

    SciTech Connect

    He, Jiayue; Lu, Lu; Zhao, Chen; Mei, Donghai; Lercher, Johannes A.

    2014-03-01

    Catalytic pathways for the cleavage of ether bonds in benzyl phenyl ether (BPE) in liquid phase using Ni- and zeolite-based catalysts are explored. In the absence of catalysts, the C-O bond is selectively cleaved in water by hydrolysis, forming phenol and benzyl alcohol as intermediates, followed by alkylation. The hydronium ions catalyzing the reactions are provided by the dissociation of water at 523 K. Upon addition of HZSM-5, rates of hydrolysis and alkylation are markedly increased in relation to proton concentrations. In the presence of Ni/SiO2, the selective hydrogenolysis dominates for cleaving the Caliphatic-O bond. Catalyzed by the dual-functional Ni/HZSM-5, hydrogenolysis occurs as the major route rather than hydrolysis (minor route). In apolar undecane, the non-catalytic thermal pyrolysis route dominates. Hydrogenolysis of BPE appears to be the major reaction pathway in undecane in the presence of Ni/SiO2 or Ni/HZSM-5, almost completely suppressing radical reactions. Density functional theory (DFT) calculations strongly support the proposed C-O bond cleavage mechanisms on BPE in aqueous and apolar phases. These calculations show that BPE is initially protonated and subsequently hydrolyzed in the aqueous phase. Finally, DFT calculations suggest that the radical reactions in non-polar solvents lead to primary benzyl and phenoxy radicals in undecane, which leads to heavier condensation products as long as metals are absent for providing dissociated hydrogen.

  18. Ligand-Accelerated ortho-C–H Alkylation of Arylcarboxylic Acids Using Alkyl Boron Reagents

    PubMed Central

    Thuy-Boun, Peter S.; Villa, Giorgio; Dang, Devin; Richardson, Paul; Su, Shun; Yu, Jin-Quan

    2013-01-01

    A protocol for the Pd(II)-catalyzed ortho-C–H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Mono-protected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated. PMID:24124892

  19. Some Rearrangements of Free Alkyl Radicals and Alkyl Cations in Solutions

    NASA Astrophysics Data System (ADS)

    Reutov, Oleg A.

    1984-03-01

    The results of studies of rearrangement reactions by the author and his co-workers during the last 20 years are described. A rearrangement of the n-propyl free radical in solutions as a result of the hydrogen 1,3-shift has been discovered and its characteristic features have been investigated (using carbon-14, deuterium, and tritium). The reaction involving the formation of organomercury compounds from mercury salts of carboxylic acids and peroxides has been studied and a mechanism has been proposed for it. New skeletal rearrangements in the thermal decomposition of cycloalkyl peroxides in benzene and bromoform have been discovered. It has been shown by the method of double 13C NMR that some of the reactions involve the formation of species which manifest properties intermediate between those of free radicals and carbonium ions. The mechanism of the thermolysis of peroxides is considered. The skeletal rearrangements and hydride shifts in the deamination and solvolysis of alicyclic compounds have been studied and a number of rearrangements with 1,2-migration of the halogen and in particular the isomerisation of acyloxybromopropanes in organic solvents, which takes place particularly readily, have been observed. The bibliography includes 103 references.

  20. Synthesis of 2-phenyl-4,5-substituted oxazoles by copper-catalyzed intramolecular cyclization of functionalized enamides.

    PubMed

    Vijay Kumar, S; Saraiah, B; Misra, N C; Ila, H

    2012-12-07

    An efficient two-step synthesis of 2-phenyl-4,5-substituted oxazoles involving intramolecular copper-catalyzed cyclization of highly functionalized novel β-(methylthio)enamides as the key step has been reported. These enamides are obtained by nucleophilic ring-opening of newly synthesized 4-[(methylthio)hetero(aryl)methylene]-2-phenyl-5-oxazolone precursors by alkoxides, amines, amino acid esters and aryl/alkyl Grignard reagents, thus leading to the introduction of an ester, N-substituted carboxamide or acyl functionalities at 4-position of the product oxazoles. Synthesis of two naturally occurring 2,5-diaryloxazoles, i.e., texamine and uguenenazole, via two-step hydrolysis-decarboxylation of the corresponding 2,5-diaryloxazole-4-carboxylates has also been described. Similarly, three of the serine-derived oxazole-4-carboxamides were elaborated to novel trisubstituted 4,2'-bisoxazoles through DAST/DBU-mediated cyclodehydration-dehydrohalogenation sequence. The present protocol is complementary and an improvement to our previously reported silver carbonate-induced cyclization of β-bis(methylthio)enamides to 2-phenyl-5-(methylthio)-4-substituted oxazoles.

  1. Alkylation of isobutane with light olefins: Yields of alkylates for different olefins

    SciTech Connect

    Albright, L.F.; Kranz, K.E.; Masters, K.R.

    1993-12-01

    For alkylation of isobutane with C{sub 3}-C{sub 5} olefins using sulfuric acid as the catalyst, the yields of alkylates with different olefins are compared as the operating conditions are changed. The results of recent pilot plant experiments with propylene, C{sub 4} olefins, and C{sub 5} olefins permit such comparisons. The yields expressed as weight of alkylate produced per 100 wt of olefin consumed varied from about 201:100 to 220:100. Weight ratios of the isobutane consumed per olefin consumed vary from about 101:100 to 120:100. differences of yield values are explained by the changes in the overall chemistry. The procedure employed to calculate yields with good accuracy is based on the analysis of the alkylate and the amount of conjunct polymers produced. Based on literature data, yields are also reported for alkylations using HF as the catalyst.

  2. Palladium-Catalyzed Arylation of Alkyl Sulfenate Anions.

    PubMed

    Jia, Tiezheng; Zhang, Mengnan; Jiang, Hui; Wang, Carol Y; Walsh, Patrick J

    2015-11-04

    A unique palladium-catalyzed arylation of alkyl sulfenate anions is introduced that affords aryl alkyl sulfoxides in high yields. Due to the base sensitivity of the starting sulfoxides, sulfenate anion intermediates, and alkyl aryl sulfoxide products, the use of a mild method to generate alkyl sulfenate anions was crucial to the success of this process. Thus, a fluoride triggered elimination strategy was employed with alkyl 2-(trimethylsilyl)ethyl sulfoxides to liberate the requisite alkyl sulfenate anion intermediates. In the presence of palladium catalysts with bulky monodentate phosphines (SPhos and Cy-CarPhos) and aryl bromides or chlorides, alkyl sulfenate anions were readily arylated. Moreover, the thermal fragmentation and the base promoted elimination of alkyl sulfoxides was overridden. The alkyl sulfenate anion arylation exhibited excellent chemoselectivity in the presence of functional groups, such as anilines and phenols, which are also known to undergo palladium catalyzed arylation reactions.

  3. Alkyl phosphonic acids and sulfonic acids in the Murchison meteorite

    NASA Technical Reports Server (NTRS)

    Cooper, George W.; Onwo, Wilfred M.; Cronin, John R.

    1992-01-01

    Homologous series of alkyl phosphonic acids and alkyl sulfonic acids, along with inorganic orthophosphate and sulfate, are identified in water extracts of the Murchison meteorite after conversion to their t-butyl dimethylsilyl derivatives. The methyl, ethyl, propyl, and butyl compounds are observed in both series. Five of the eight possible alkyl phosphonic acids and seven of the eight possible alkyl sulfonic acids through C4 are identified. Abundances decrease with increasing carbon number as observed of other homologous series indigenous to Murchison. Concentrations range downward from approximately 380 nmol/gram in the alkyl sulfonic acid series, and from 9 nmol/gram in the alkyl phosphonic acid series.

  4. Chiral Alkyl Halides: Underexplored Motifs in Medicine

    PubMed Central

    Gál, Bálint; Bucher, Cyril; Burns, Noah Z.

    2016-01-01

    While alkyl halides are valuable intermediates in synthetic organic chemistry, their use as bioactive motifs in drug discovery and medicinal chemistry is rare in comparison. This is likely attributable to the common misconception that these compounds are merely non-specific alkylators in biological systems. A number of chlorinated compounds in the pharmaceutical and food industries, as well as a growing number of halogenated marine natural products showing unique bioactivity, illustrate the role that chiral alkyl halides can play in drug discovery. Through a series of case studies, we demonstrate in this review that these motifs can indeed be stable under physiological conditions, and that halogenation can enhance bioactivity through both steric and electronic effects. Our hope is that, by placing such compounds in the minds of the chemical community, they may gain more traction in drug discovery and inspire more synthetic chemists to develop methods for selective halogenation. PMID:27827902

  5. Epoxy resin cure. [Phenyl glycidyl ether

    SciTech Connect

    Smith, R.E.; Woodburn, G.L.

    1986-07-01

    The reactions that occur between the model epoxy, phenyl glycidyl ether, and the cure agent dicyandiamide (DICY) have been investigated using nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR), gel permeation chromatography (GPC), and high-performance liquid chromatography (HPLC) techniques. It is shown that the reaction at 130/sup 0/C requires 90 min for completion when catalyzed by boron trifluoride monoethyl amine (BF/sub 3/-MEA). At least three major products are formed. The identity of these products is based on previously published spectroscopic data. 3 refs., 5 figs.

  6. Chemistry of polycyclic aromatic hydrocarbons formation from phenyl radical pyrolysis and reaction of phenyl and acetylene.

    PubMed

    Comandini, A; Malewicki, T; Brezinsky, K

    2012-03-15

    An experimental investigation of phenyl radical pyrolysis and the phenyl radical + acetylene reaction has been performed to clarify the role of different reaction mechanisms involved in the formation and growth of polycyclic aromatic hydrocarbons (PAHs) serving as precursors for soot formation. Experiments were conducted using GC/GC-MS diagnostics coupled to the high-pressure single-pulse shock tube present at the University of Illinois at Chicago. For the first time, comprehensive speciation of the major stable products, including small hydrocarbons and large PAH intermediates, was obtained over a wide range of pressures (25-60 atm) and temperatures (900-1800 K) which encompass the typical conditions in modern combustion devices. The experimental results were used to validate a comprehensive chemical kinetic model which provides relevant information on the chemistry associated with the formation of PAH compounds. In particular, the modeling results indicate that the o-benzyne chemistry is a key factor in the formation of multi-ring intermediates in phenyl radical pyrolysis. On the other hand, the PAHs from the phenyl + acetylene reaction are formed mainly through recombination between single-ring aromatics and through the hydrogen abstraction/acetylene addition mechanism. Polymerization is the common dominant process at high temperature conditions.

  7. Transition metal-free decarboxylative alkylation reactions.

    PubMed

    Liu, Ping; Zhang, Guanghui; Sun, Peipei

    2016-11-22

    This review summarizes advances in the decarboxylative alkylation of carboxylic acids and their derivatives under transition metal-free conditions in recent years. Unlike most transition metal-catalyzed decarboxylative coupling reactions which tend to undergo catalytic cycles, the mechanisms of reactions under metal-free conditions are usually diverse and even ambiguous in some cases. This article offers an overview of reaction types and their corresponding mechanisms, highlights some of the advantages and limitations, and focuses on introducing UV and visible light-induced, organocatalyst and peroxide promoted radical processes for decarboxylative alkylation and the formation of C-C bonds.

  8. Alkyl ferulates in wound healing potato tubers.

    PubMed

    Bernards, M A; Lewis, N G

    1992-10-01

    Seven ferulic acid esters of 1-alkanols ranging in carbon length from C16 to C28 were synthesized and an HPLC protocol for their separation developed. Extracts prepared from wound healing potato (Solanum tuberosum) tubers and analysed by HPLC indicated that alkyl ferulate esters begin to accumulate 3-7 days after wound treatment. Of the nine esters identified by EIMS, (including two esters of odd chain length alkanols) hexadecyl and octadecyl ferulates were predominant. Alkyl ferulate esters were restricted to the wound periderm.

  9. Enhancement of alkylation catalysts for improved supercritical fluid regeneration

    DOEpatents

    Ginosar, Daniel M.; Petkovic, Lucia

    2009-09-22

    A method of modifying an alkylation catalyst to reduce the formation of condensed hydrocarbon species thereon. The method comprises providing an alkylation catalyst comprising a plurality of active sites. The plurality of active sites on the alkylation catalyst may include a plurality of weakly acidic active sites, intermediate acidity active sites, and strongly acidic active sites. A base is adsorbed to a portion of the plurality of active sites, such as the strongly acidic active sites, selectively poisoning the strongly acidic active sites. A method of modifying the alkylation catalyst by providing an alkylation catalyst comprising a pore size distribution that sterically constrains formation of the condensed hydrocarbon species on the alkylation catalyst or by synthesizing the alkylation catalyst to comprise a decreased number of strongly acidic active sites is also disclosed, as is a method of improving a regeneration efficiency of the alkylation catalyst.

  10. Enhancement of alkylation catalysts for improved supercritical fluid regeneration

    DOEpatents

    Ginosar, Daniel M.; Petkovic, Lucia M.

    2010-12-28

    A method of modifying an alkylation catalyst to reduce the formation of condensed hydrocarbon species thereon. The method comprises providing an alkylation catalyst comprising a plurality of active sites. The plurality of active sites on the alkylation catalyst may include a plurality of weakly acidic active sites, intermediate acidity active sites, and strongly acidic active sites. A base is adsorbed to a portion of the plurality of active sites, such as the strongly acidic active sites, selectively poisoning the strongly acidic active sites. A method of modifying the alkylation catalyst by providing an alkylation catalyst comprising a pore size distribution that sterically constrains formation of the condensed hydrocarbon species on the alkylation catalyst or by synthesizing the alkylation catalyst to comprise a decreased number of strongly acidic active sites is also disclosed, as is a method of improving a regeneration efficiency of the alkylation catalyst.

  11. 40 CFR 721.5960 - N,N′-Bis(2-(2-(3-alkyl)thia- zoline) vinyl)-1,4-pheny-lene-dia-mine methyl sulfate double salt...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... substance identified generically as N,N′-Bis(2-(2-(3-alkyl)-thi-a-zo-line)vinyl)-1,4-phenyl-ene-di-a-mine...), (f) (concentration set at 1 percent), (g)(1)(iii), (g)(1), (may be lethal if inhaled or in contact with eyes), (g)(2)(i), (g)(2)(ii), (g)(2)(iv), (g)(2)(v), and (g)(5). The provision of §...

  12. 40 CFR 721.5960 - N,N′-Bis(2-(2-(3-alkyl)thia- zoline) vinyl)-1,4-pheny-lene-dia-mine methyl sulfate double salt...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... substance identified generically as N,N′-Bis(2-(2-(3-alkyl)-thi-a-zo-line)vinyl)-1,4-phenyl-ene-di-a-mine...), (f) (concentration set at 1 percent), (g)(1)(iii), (g)(1), (may be lethal if inhaled or in contact with eyes), (g)(2)(i), (g)(2)(ii), (g)(2)(iv), (g)(2)(v), and (g)(5). The provision of §...

  13. 40 CFR 721.5960 - N,N′-Bis(2-(2-(3-alkyl)thia- zoline) vinyl)-1,4-pheny-lene-dia-mine methyl sulfate double salt...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... substance identified generically as N,N′-Bis(2-(2-(3-alkyl)-thi-a-zo-line)vinyl)-1,4-phenyl-ene-di-a-mine...), (f) (concentration set at 1 percent), (g)(1)(iii), (g)(1), (may be lethal if inhaled or in contact with eyes), (g)(2)(i), (g)(2)(ii), (g)(2)(iv), (g)(2)(v), and (g)(5). The provision of §...

  14. Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity.

    PubMed

    Kashima, Kenichi; Teraoka, Kota; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken

    2016-05-06

    Axially chiral 3-(2-halophenyl)pyridines were successfully synthesized in high yields with excellent enantioselectivity by the cationic rhodium(I)/(S)-H8-BINAP complex-catalyzed atroposelective [2 + 2 + 2] cycloaddition of (o-halophenyl)diynes with nitriles. Interestingly, regio- and enantioselectivity highly depend on ortho substituents on the phenyl group of diynes. When the ortho substituents were methoxy and methoxycarbonyl groups, axially chiral 3-arylpyridines were obtained as a major product, while enantioselectivity was lowered significantly. On the other hand, when the ortho substituents were alkyl groups, regioselectivity was switched to give achiral 6-arylpyridines in high yields.

  15. Transducer influence of polycyclic aromatic hydrocarbons (PAHs) on photoisomerisation of 1-alkyl-2-(arylazo)imidazoles

    NASA Astrophysics Data System (ADS)

    Gayen, Pallab; Sinha, Chittaranjan

    2013-03-01

    The UV light irradiation to a solution of 1-alkyl-2-(arylazo)imidazole (L) in toluene shows transformation of trans to cis configuration about sbnd Ndbnd Nsbnd bond. The rate of photo-isomerisation and quantum yields are influenced by internal parameters like - nature of substituents, coordination to metal ions, steric and electronic effect, protonation etc. and the external factors like solvent (polarity, viscosity, dipole moment etc.), presence of innocent (to be chemically noninteracting) and noninnocent (chemically interacting) ions or molecules. In this work the influence of polycyclic aromatic hydrocarbons (PAH) such as - napththalene, anthracene, phenanthrene, pyrene - an innocent system, on the photochromic efficiency of L has been examined. The PAHs are π-donor and may form a π-π continuum with L which can significantly affect the motional (vibration, rotation) properties of the analyte and hence the photochromic activity. The rate and quantum yield of trans-to-cis isomerisation of L decrease with increasing [PAH] and also with increasing number of the fused phenyl ring(s) in PAH. Thus the photoisomerisation follows the rate sequence: no PAH > napththalene > anthracene-phenanthrene > pyrene. The reverse change, cis-to-trans is very slow upon light irradiation while appreciably fast in thermal process at dark. The activation energy (Ea) also decreases with [PAH] and number of fused phenyl rings.

  16. 40 CFR 721.2420 - Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., alkyl sulfate salt. 721.2420 Section 721.2420 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2420 Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt. (a... generically as an alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt (PMN P-91-288) is subject...

  17. 40 CFR 721.2410 - Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., alkyl sulfate salts. 721.2410 Section 721.2410 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2410 Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts. (a... generically as alkoxylated dialkyldiethylenetriamine, alkyl sulfate salts (PMN P-94-325, 326, and 327)...

  18. 40 CFR 721.2420 - Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., alkyl sulfate salt. 721.2420 Section 721.2420 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2420 Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt. (a... generically as an alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt (PMN P-91-288) is subject...

  19. 40 CFR 721.2410 - Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., alkyl sulfate salts. 721.2410 Section 721.2410 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2410 Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts. (a... generically as alkoxylated dialkyldiethylenetriamine, alkyl sulfate salts (PMN P-94-325, 326, and 327)...

  20. IONIC LIQUID-CATALYZED ALKYLATION OF ISOBUTANE WITH 2-BUTENE

    EPA Science Inventory

    A detailed study of the alkylation of isobutane with 2-butene in ionic liquid media has been conducted using 1-alkyl-3-methylimidazolium halides?aluminum chloride encompassing various alkyl groups (butyl-, hexyl-, and octyl-) and halides (Cl, Br, and I) on its cations and anions,...

  1. 40 CFR 721.2825 - Alkyl ester (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl ester (generic name). 721.2825... Substances § 721.2825 Alkyl ester (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance alkyl ester (PMN P-84-968) is subject to reporting under this...

  2. 40 CFR 721.2825 - Alkyl ester (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkyl ester (generic name). 721.2825... Substances § 721.2825 Alkyl ester (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance alkyl ester (PMN P-84-968) is subject to reporting under this...

  3. 40 CFR 721.2825 - Alkyl ester (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl ester (generic name). 721.2825... Substances § 721.2825 Alkyl ester (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance alkyl ester (PMN P-84-968) is subject to reporting under this...

  4. 40 CFR 721.2825 - Alkyl ester (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl ester (generic name). 721.2825... Substances § 721.2825 Alkyl ester (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance alkyl ester (PMN P-84-968) is subject to reporting under this...

  5. 40 CFR 721.2825 - Alkyl ester (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl ester (generic name). 721.2825... Substances § 721.2825 Alkyl ester (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance alkyl ester (PMN P-84-968) is subject to reporting under this...

  6. 40 CFR 721.10233 - Linear alkyl epoxide (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Linear alkyl epoxide (generic). 721... Substances § 721.10233 Linear alkyl epoxide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as linear alkyl epoxide (PMN...

  7. 40 CFR 721.10233 - Linear alkyl epoxide (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Linear alkyl epoxide (generic). 721... Substances § 721.10233 Linear alkyl epoxide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as linear alkyl epoxide (PMN...

  8. 40 CFR 721.10233 - Linear alkyl epoxide (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Linear alkyl epoxide (generic). 721... Substances § 721.10233 Linear alkyl epoxide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as linear alkyl epoxide (PMN...

  9. 40 CFR 721.4136 - Alkyl heteropolycyclic-aniline (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl heteropolycyclic-aniline... Specific Chemical Substances § 721.4136 Alkyl heteropolycyclic-aniline (generic). (a) Chemical substance... alkyl heteropolycyclic-aniline (PMN P-00-0067) is subject to reporting under this section for...

  10. 40 CFR 721.5769 - Mixture of nitrated alkylated phenols.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Mixture of nitrated alkylated phenols... Substances § 721.5769 Mixture of nitrated alkylated phenols. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a mixture of nitrated alkylated...

  11. 40 CFR 721.5769 - Mixture of nitrated alkylated phenols.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Mixture of nitrated alkylated phenols... Substances § 721.5769 Mixture of nitrated alkylated phenols. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a mixture of nitrated alkylated...

  12. 40 CFR 721.5769 - Mixture of nitrated alkylated phenols.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Mixture of nitrated alkylated phenols... Substances § 721.5769 Mixture of nitrated alkylated phenols. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a mixture of nitrated alkylated...

  13. 40 CFR 721.5769 - Mixture of nitrated alkylated phenols.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Mixture of nitrated alkylated phenols... Substances § 721.5769 Mixture of nitrated alkylated phenols. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a mixture of nitrated alkylated...

  14. 40 CFR 721.5769 - Mixture of nitrated alkylated phenols.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Mixture of nitrated alkylated phenols... Substances § 721.5769 Mixture of nitrated alkylated phenols. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a mixture of nitrated alkylated...

  15. 40 CFR 721.10699 - Polyfluorinated alkyl thio acrylamide (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Polyfluorinated alkyl thio acrylamide... Specific Chemical Substances § 721.10699 Polyfluorinated alkyl thio acrylamide (generic). (a) Chemical... as polyfluorinated alkyl thio acrylamide (PMN P-11-529) is subject to reporting under this...

  16. 40 CFR 721.2410 - Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., alkyl sulfate salts. 721.2410 Section 721.2410 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2410 Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts. (a... generically as alkoxylated dialkyldiethylenetriamine, alkyl sulfate salts (PMN P-94-325, 326, and 327)...

  17. 40 CFR 721.2420 - Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ..., alkyl sulfate salt. 721.2420 Section 721.2420 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2420 Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt. (a... generically as an alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt (PMN P-91-288) is subject...

  18. 40 CFR 721.2410 - Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ..., alkyl sulfate salts. 721.2410 Section 721.2410 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2410 Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts. (a... generically as alkoxylated dialkyldiethylenetriamine, alkyl sulfate salts (PMN P-94-325, 326, and 327)...

  19. 40 CFR 721.2420 - Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., alkyl sulfate salt. 721.2420 Section 721.2420 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2420 Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt. (a... generically as an alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt (PMN P-91-288) is subject...

  20. 40 CFR 721.2420 - Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ..., alkyl sulfate salt. 721.2420 Section 721.2420 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2420 Alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt. (a... generically as an alkoxylated dialkyldiethylenetriamine, alkyl sulfate salt (PMN P-91-288) is subject...

  1. 40 CFR 721.2410 - Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ..., alkyl sulfate salts. 721.2410 Section 721.2410 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.2410 Alkoxylated alkyldiethylenetriamine, alkyl sulfate salts. (a... generically as alkoxylated dialkyldiethylenetriamine, alkyl sulfate salts (PMN P-94-325, 326, and 327)...

  2. Copper-catalyzed radical carbooxygenation: alkylation and alkoxylation of styrenes.

    PubMed

    Liao, Zhixiong; Yi, Hong; Li, Zheng; Fan, Chao; Zhang, Xu; Liu, Jie; Deng, Zixin; Lei, Aiwen

    2015-01-01

    A simple copper-catalyzed direct radical carbooxygenation of styrenes is developed utilizing alkyl bromides as radical resources. This catalytic radical difunctionalization accomplishes both alkylation and alkoxylation of styrenes in one pot. A broad range of styrenes and alcohols are well tolerated in this transformation. The EPR experiment shows that alkyl halides could oxidize Cu(I) to Cu(II) in this transformation.

  3. 40 CFR 721.1878 - Alkali metal alkyl borohydride (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkali metal alkyl borohydride... Specific Chemical Substances § 721.1878 Alkali metal alkyl borohydride (generic). (a) Chemical substance... alkali metal alkyl borohydride (PMN P-00-1089) is subject to reporting under this section for...

  4. 40 CFR 721.1878 - Alkali metal alkyl borohydride (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkali metal alkyl borohydride... Specific Chemical Substances § 721.1878 Alkali metal alkyl borohydride (generic). (a) Chemical substance... alkali metal alkyl borohydride (PMN P-00-1089) is subject to reporting under this section for...

  5. 40 CFR 721.1878 - Alkali metal alkyl borohydride (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkali metal alkyl borohydride... Specific Chemical Substances § 721.1878 Alkali metal alkyl borohydride (generic). (a) Chemical substance... alkali metal alkyl borohydride (PMN P-00-1089) is subject to reporting under this section for...

  6. 40 CFR 721.1878 - Alkali metal alkyl borohydride (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkali metal alkyl borohydride... Specific Chemical Substances § 721.1878 Alkali metal alkyl borohydride (generic). (a) Chemical substance... alkali metal alkyl borohydride (PMN P-00-1089) is subject to reporting under this section for...

  7. 40 CFR 721.1878 - Alkali metal alkyl borohydride (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkali metal alkyl borohydride... Specific Chemical Substances § 721.1878 Alkali metal alkyl borohydride (generic). (a) Chemical substance... alkali metal alkyl borohydride (PMN P-00-1089) is subject to reporting under this section for...

  8. Poly(ethyleneoxide) functionalization through alkylation

    DOEpatents

    Sivanandan, Kulandaivelu; Eitouni, Hany Basam; Li, Yan; Pratt, Russell Clayton

    2015-04-21

    A new and efficient method of functionalizing high molecular weight polymers through alkylation using a metal amide base is described. This novel procedure can also be used to synthesize polymer-based macro-initiators containing radical initiating groups at the chain-ends for synthesis of block copolymers.

  9. Synthesis and characterization of chitosan alkyl urea.

    PubMed

    Wang, Jing; Jiang, Ji-Zhou; Chen, Wei; Bai, Zheng-Wu

    2016-07-10

    Chitosan is a versatile material employed for various purposes in many fields including the development of chiral stationary phases for enantioseparation. Chitosan alkyl urea is a kind of intermediate used to prepare enantioseparation materials. In order to synthesize the intermediates, in the present work, a new way to prepare chitosan alkyl urea has been established: chitosan was first reacted with methyl chloroformate yielding N-methoxyformylated chitosan, which was then converted to chitosan alkyl urea through amine-ester exchange reaction. With a large excess of methyl chloroformate and primary amine of low stereohindrance, the amino group in chitosan could be almost completely converted to ureido group. The as-prepared chitosan alkyl urea derivatives were characterized by IR, (1)H NMR, (13)C NMR,(1)H-(1)H COSY and (1)H-(13)C HSQC NMR spectra. The chemical shifts of hydrogen and carbon atoms of glucose unit were assigned. It was found that the degree of substitution was obviously lower if cyclopropyl amine, aniline, tert-butyl amine and diethyl amine were used as reactants for the amine-ester exchange reaction. The reason was explained with the aid of theoretical calculations.

  10. 77 FR 72747 - Alkyl(C8

    Federal Register 2010, 2011, 2012, 2013, 2014

    2012-12-06

    ... Classification System (NAICS) codes is not intended to be exhaustive, but rather provides a guide to help readers.../reproductive screening test (OECD 422) toxicity study on a representative N- alkyl(C 8 -C 18... in the reproductive or developmental parameters examined. No systemic toxicity was observed in...

  11. Synthesis of Phenyl-Adducted Cyclodextrin through the Click Reaction

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A new derivative of ß-cyclodextrin (CD) has been made incorporating the phenyl group through the use of click reaction. The resulting product exhibits a self-association phenomenon through the formation of inclusion compound between the phenyl group and CD. The product has been characterized by 1H...

  12. Effects of alkyl chain length on properties of 1-alkyl-3-methylimidazolium fluorohydrogenate ionic liquid crystals.

    PubMed

    Xu, Fei; Matsumoto, Kazuhiko; Hagiwara, Rika

    2010-11-15

    A series of 1-alkyl-3-methylimidazolium fluorohydrogenate salts (C(x)MIm(FH)(2)F, x=8, 10, 12, 14, 16, and 18) have been characterized by thermal analysis, polarized optical microscopy, IR spectroscopy, X-ray diffraction, and anisotropic ionic conductivity measurements. Liquid crystalline mesophases with a smectic A interdigitated bilayer structure are observed from C(10) to C(18), showing a fan-like or focal conic texture. The temperature range of the mesophase increases with the increase in the alkyl chain length (from 10.1 °C for C(10)MIm(FH)(2)F to 123.1 °C for C(18)MIm(FH)(2)F). The distance between the two layers in the smectic structure gradually increases with increasing alkyl chain length and decreases with increasing temperature. Conductivity parallel to the smectic layers is around 10 mS cm(-1) regardless of the alkyl chain length, whereas that perpendicular to the smectic layers decreases with increasing alkyl chain length because of the thicker insulating sheet with the longer alkyl chain.

  13. Synthesis and evaluation of tamoxifen derivatives with a long alkyl side chain as selective estrogen receptor down-regulators.

    PubMed

    Shoda, Takuji; Kato, Masashi; Harada, Rintaro; Fujisato, Takuma; Okuhira, Keiichiro; Demizu, Yosuke; Inoue, Hideshi; Naito, Mikihiko; Kurihara, Masaaki

    2015-07-01

    Estrogen receptors (ERs) play a major role in the growth of human breast cancer cells. An antagonist that acts as not only an inhibitor of ligand binding but also an inducer of the down-regulation of ER would be useful for the treatment for ER-positive breast cancer. We previously reported the design and synthesis of a selective estrogen receptor down-regulator (SERD), (E/Z)-4-(1-{4-[2-(dodecylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenol (C12), which is a tamoxifen derivative having a long alkyl chain on the amine moiety. This compound induced degradation of ERα via a proteasome-dependent pathway and showed an antagonistic effect in MCF-7 cells. With the aim of increasing the potency of SERDs, we designed and synthesized various tamoxifen derivatives that have various lengths and terminal groups of the long alkyl side chain. During the course of our investigation, C10F having a 10-fluorodecyl group on the amine moiety of 4-OHT was shown to be the most potent compound among the tamoxifen derivatives. Moreover, computational docking analysis suggested that the long alkyl chain interacted with the hydrophobic region on the surface of the ER, which is a binding site of helix 12 and coactivator. These results provide useful information to develop promising candidates as SERDs.

  14. Corrosion abatement in sulfuric acid alkylation unit horizontal contactors

    SciTech Connect

    Schutt, H.U.

    1997-09-01

    The need to increase throughput in alkylation plants has resulted in higher operating temperatures and higher water levels in alkylation acids than projected by design. Combined with higher flow rates, the more severe process environment causes carbon steel to corrode at increased rates. Carbon steel is the main material of construction for horizontal contactors (Stratco reactors). A leak to the atmosphere in the hydraulic end cone of one contactor and the realization that basic corrosion data are not available for high throughput process conditions in alkylation units prompted a laboratory study to develop the lacking expertise. Corrosion in alkylation unit horizontal contactors is successfully mitigated by saturating fresh alkylation acid with ferrous sulfate.

  15. The effect of bromine scanning around the phenyl group of 4-phenyl­quinolone derivatives

    PubMed Central

    Steiger, Scott A.; Monacelli, Anthony J.; Li, Chun; Hunting, Janet L.; Natale, Nicholas R.

    2014-01-01

    Three quinolone compounds were synthesized and crystallized in an effort to study the structure–activity relationship of these calcium-channel antagonists. In all three quinolones, viz. ethyl 4-(4-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate, (I), ethyl 4-(3-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-car­box­yl­ate, (II), and ethyl 4-(2-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate, (III), all C21H24BrNO3, common structural features such as a flat boat conformation of the 1,4-di­hydro­pyridine (1,4-DHP) ring, an envelope conformation of the fused cyclo­hexa­none ring and a bromo­phenyl ring at the pseudo-axial position and orthogonal to the 1,4-DHP ring are retained. However, due to the different packing inter­actions in each compound, halogen bonds are observed in (I) and (III). Compound (III) crystallizes with two molecules in the asymmetric unit. All of the prepared derivatives satisfy the basic structural requirements to possess moderate activity as calcium-channel antagonists. PMID:25093361

  16. Searches for new alkylation catalysts, processes forge ahead

    SciTech Connect

    Rhodes, A.

    1994-08-22

    As a result of the hazardous properties of hydrofluoric acid (HF), HF alkylation has been the subject of much recent controversy. The safety and environmental requirements associated with the HF alkylation processes continue to drive industry to develop new alkylation technologies. In fact, several major process licensors are well on their ways to bringing these new technologies to market. The new alkylation processes under development center around new, less-harmful catalysts. Although this work is progressing rapidly, an update of the status of some of these new processes will keep refiners abreast of the new options they may soon have for building new alkylation units or retrofitting existing ones. The process development and economics are described for a Topsoe/Kellogg fixed bed alkylation process and the Kerr-McGee homogeneous alkylation technology process.

  17. Phenyl Benzo[b]phenothiazine as a Visible Light Photoredox Catalyst for Metal-Free Atom Transfer Radical Polymerization.

    PubMed

    Dadashi-Silab, Sajjad; Pan, Xiangcheng; Matyjaszewski, Krzysztof

    2016-12-23

    This paper reports use of phenyl benzo[b]phenothiazine (Ph-benzoPTZ) as a visible light-induced metal-free atom transfer radical polymerization (ATRP) photoredox catalyst. Well-controlled polymerizations of various methacrylate monomers were conducted under a 392 nm visible light LED using Ph-benzoPTZ to activate different alkyl halides. The use of the photocatalyst enabled temporal control over the growth of polymer chains during intermittent on/off periods. The polymerization was initiated and progressed only under stimulation by light and completely stopped in the absence of light. Block copolymers were synthesized to demonstrate high retention of chain end fidelity in the polymers and livingness of the process.

  18. PROCESS FOR PRODUCING ALKYL ORTHOPHOSPHORIC ACID EXTRACTANTS

    DOEpatents

    Grinstead, R.R.

    1962-01-23

    A process is given for producing superior alkyl orthophosphoric acid extractants for use in solvent extraction methods to recover and purify various metals such as uranium and vanadium. The process comprises slurrying P/sub 2/O/ sub 5/ in a solvent diluent such as kerosene, benzene, isopropyl ether, and the like. An alipbatic alcohol having from nine to seventeen carbon atoms, and w- hcrein ihc OH group is situated inward of the terminal carbon atoms, is added to the slurry while the reaction temperature is mainiained below 60 deg C. The alcohol is added in the mole ratio of about 2 to l, alcohol to P/sub 2/O/sub 5/. A pyrophosphate reaotion product is formed in the slurry-alcohol mixture. Subsequently, the pyrophosphate reaction product is hydrolyzed with dilute mineral acid to produce the desired alkyl orthophosphoric aeid extractant. The extraetant may then be separated and utilized in metal-recovery, solvent- extraction processes. (AEC)

  19. In pursuit of homoleptic actinide alkyl complexes.

    PubMed

    Seaman, Lani A; Walensky, Justin R; Wu, Guang; Hayton, Trevor W

    2013-04-01

    This Forum Article describes the pursuit of isolable homoleptic actinide alkyl complexes, starting with the pioneering work of Gilman during the Manhattan project. The initial reports in this area suggested that homoleptic uranium alkyls were too unstable to be isolated, but Wilkinson demonstrated that tractable uranium alkyls could be generated by purposeful "ate" complex formation, which serves to saturate the uranium coordination sphere and provide the complexes with greater kinetic stability. More recently, we reported the solid-state molecular structures of several homoleptic uranium alkyl complexes, including [Li(THF)4][U(CH2(t)Bu)5], [Li(TMEDA)]2[UMe6], [K(THF)]3[K(THF)2][U(CH2Ph)6]2, and [Li(THF)4][U(CH2SiMe3)6], by employing Wilkinson's strategy. Herein, we describe our attempts to extend this chemistry to thorium. The treatment of ThCl4(DME)2 with 5 equiv of LiCH2(t)Bu or LiCH2SiMe3 at -25 °C in THF affords [Th(CH2(t)Bu)5] (1) and [Li(DME)2][Th(CH2SiMe3)5 (2), respectively, in moderate yields. Similarly, the treatment of ThCl4(DME)2 with 6 equiv of K(CH2Ph) produces [K(THF)]2[Th(CH2Ph)6] (3), in good yield. Complexes 1-3 have been fully characterized, while the structures of 1 and 3 were confirmed by X-ray crystallography. Additionally, the electronic properties of 1 and 3 were explored by density functional theory.

  20. Soluble Alkyl Substituted Polygermanes. Thermochromic Behavior.

    DTIC Science & Technology

    1986-07-17

    are strongly thermochromic . The effect is attributed to conformational locking of the backbone which is caused by the crystallization of the side groups...are strongly thermochromic . The effect is attributed to the conformational locking of the backbone which is caused by the crystallization of the side...SYMBOL. 02 &m A -- .- h.. .. .. . . . . . . . . ... . . . .. RJ 5008 (52258) 1/24/86 Chemis try SOLUBLE ALKYL SUBSTITUTED POLYGERMANES: THERMOCHROMIC

  1. ALKYL PYROPHOSPHATE METAL SOLVENT EXTRACTANTS AND PROCESS

    DOEpatents

    Long, R.L.

    1958-09-30

    A process is presented for the recovery of uranium from aqueous mineral acidic solutions by solvent extraction. The extractant is a synmmetrical dialkyl pyrophosphate in which the alkyl substituents have a chain length of from 4 to 17 carbon atoms. Mentioned as a preferred extractant is dioctyl pyrophosphate. The uranium is precipitated irom the organic extractant phase with an agent such as HF, fluoride salts. alcohol, or ammonia.

  2. Bis (4-(3,4-dimethylene-pyrrolidyl)-phenyl) methane

    NASA Technical Reports Server (NTRS)

    Ottenbrite, Raphael M. (Inventor)

    1990-01-01

    The primary objective is to prepare high temperature polymeric materials, especially linear aromatic polyimides, which maintain their integrity and toughness during long exposure times at elevated temperatures. The attained benefits are obtained by first providing the bis (exocyclodiene) bis (4-(3,4-dimethylene-pyrrolidyl)-phenyl) methane, which is a novel material formed from the monomer N-phenyl-3,4-dimethylene-pyrrolidine. This compound undergoes Diels-Alder reaction with a bismaleimide, without the evolution of gaseous by-products, to form the aromatic polyimide bis (4-(3,4-dimethylene-pyrrolidyl)-phenyl) methane.

  3. The Scarlet Letter of Alkylation: A Mini Review of Selective Alkylating Agents

    PubMed Central

    Oronsky, Bryan T; Reid, Tony; Knox, Susan J; Scicinski, Jan J

    2012-01-01

    If there were a stigma scale for chemotherapy, alkylating agents would be ranked at the top of the list. The chemical term alkylation is associated with nonselective toxicity, an association that dates back to the use of nitrogen mustards during World War I as chemical warfare agents. That this stigma persists and extends to compounds that, through selectivity, attempt to “tame” the indiscriminate destructive potential of alkylation is the subject of this review. Selective alkylation, as it is referred to herein, constitutes an extremely nascent and dynamic field in oncology. The pharmacodynamic response to this selective strategy depends on a delicate kinetic balance between specificity and the rate and extent of binding. Three representative compounds are presented: RRx-001, 3-bromopyruvate, and TH-302. The main impetus for the development of these compounds has been the avoidance of the serious complications of traditional alkylating agents; therefore, it is the thesis of this review that they should not experience stigma by association. PMID:22937173

  4. Tetrahydrofurfuryloxide derivatives of alkyl aluminum species.

    SciTech Connect

    Boyle, Timothy J.; Avilucea, Gabriel; Bunge, Scott D.; Alam, Todd Michael; Rodriguez, Mark Andrew; Cherry, Brian Ray; Tissot, Ralph George, Jr.; Segall, Judith M.

    2004-12-01

    Tetrahydrofurfuryl alcohol (H-OTHF) was successfully reacted with a series of aluminum alkyls (AlR{sub 3}) to yield compounds of the general formula [R{sub 2}Al({mu}-OTHF)]{sub 2} where R = CH{sub 3} (1), CH{sub 2}CH{sub 3} (2), and CH{sub 2}CH(CH{sub 3}){sub 2} (3). Further, reactivity studies showed that the alkyls for 1 were easily exchanged, forming compounds of the general formula [Me(OR)Al({mu}-OTHF)]{sub 2} where OR = OC{sub 6}H{sub 3}(Me){sub 2}-2,6 (4), OC{sub 6}H{sub 3}(CMe{sub 3}){sub 2}-2,6 (5a), and OSi(C{sub 6}H5){sub 3} (6). For 5a, reflux temperatures were required to get the full exchange; otherwise the asymmetric derivative [Me(OR)Al({mu}-OTHF){sub 2}AlMe{sub 2}] (5b) was isolated. The bulk powders of 1-6 were found to be in agreement with the crystal structures on the basis of elemental analyses and multinuclear solid state NMR studies. Multinuclear solution state NMR studies indicate that the alkyl OTHF derivatives have cis/trans isomers due to the chiral proton on the OTHF ligand.

  5. Interception and characterization of catalyst species in rhodium bis(diazaphospholane)-catalyzed hydroformylation of octene, vinyl acetate, allyl cyanide, and 1-phenyl-1,3-butadiene.

    PubMed

    Nelsen, Eleanor R; Brezny, Anna C; Landis, Clark R

    2015-11-11

    In the absence of H2, reaction of [Rh(H) (CO)2(BDP)] [BDP = bis(diazaphospholane)] with hydroformylation substrates vinyl acetate, allyl cyanide, 1-octene, and trans-1-phenyl-1,3-butadiene at low temperatures and pressures with passive mixing enables detailed NMR spectroscopic characterization of rhodium acyl and, in some cases, alkyl complexes of these substrates. For trans-1-phenyl-1,3-butadiene, the stable alkyl complex is an η(3)-allyl complex. Five-coordinate acyl dicarbonyl complexes appear to be thermodynamically preferred over the four-coordinate acyl monocarbonyls at low temperatures and one atmosphere of CO. Under noncatalytic (i.e., no H2 present) reaction conditions, NMR spectroscopy reveals the kinetic and thermodynamic selectivity of linear and branched acyl dicarbonyl formation. Over the range of substrates investigated, the kinetic regioselectivity observed at low temperatures under noncatalytic conditions roughly predicts the regioselectivity observed for catalytic transformations at higher temperatures and pressures. Thus, kinetic distributions of off-cycle acyl dicarbonyls constitute reasonable models for catalytic selectivity. The Wisconsin high-pressure NMR reactor (WiHP-NMRR) enables single-turnover experiments with active mixing; such experiments constitute a powerful strategy for elucidating the inherent selectivity of acyl formation and acyl hydrogenolysis in hydroformylation reactions.

  6. Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids.

    PubMed

    Huang, Ling; Su, Tao; Shan, Wenjun; Luo, Zonghua; Sun, Yang; He, Feng; Li, Xingshu

    2012-05-01

    A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC(50) value of 0.017 μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD.

  7. Aminobenzoic acid diuretics. 7. 3-Substituted 4-phenyl-, 4-arylcarbonyl-, and 4-arylmethyl-5-sulfamoylbenzoic acids and related compounds.

    PubMed

    Nielsen, O B; Bruun, H; Bretting, C; Feit, P W

    1975-01-01

    Various 4-substituted 3-alkylamino-, 3-alkoxy-, 3-alkylthio-, and 3-alkyl-5-sulfamoylbenzoic acids related to known aminobenzoic acid diuretics were synthesized and screened for their diuretic properties in dogs. The tabulated results from a 3-hr test period revealed that generally the diuretic profile and potency could be retained when 3-alkoxy, 3-alkylthio, and 3-phenethyl were substituted for the 3-alkylamino moiety. The high potency of several 3-alkoxy-, 3-alkylthio-, and 3-phenethyl-4-benzoyl-5-sulfamoylbenzoic acids confirmed previous suggestions that the apparent diuretic effect of 4- and 5-alkylamino-6-carboxy-3-phenyl-1,2-benzisothiazole 1,1-dioxides originates from the corresponding 4-benzoyl-5-sulfamoylbenzoic acid derivatives due to an existing equilibrium in plasma. 4-Benzoyl-5-sulfamoyl-3-(3-thenyloxy) benzoic acid (118) is among the most potent benzoic acid diuretics hitherto synthesized and shows significant diuretic activity in dogs at 1 mug/kg. The results obtained with different 3-substituted 4-phenyl-5-sulfamoylbenzoic acids supported the earlier concept regarding the steric influence of the 4-substituent on the diuretic potency of sulfamoylbenzoic acid diuretics.

  8. DNA-directed alkylating ligands as potential antitumor agents: sequence specificity of alkylation by intercalating aniline mustards.

    PubMed

    Prakash, A S; Denny, W A; Gourdie, T A; Valu, K K; Woodgate, P D; Wakelin, L P

    1990-10-23

    The sequence preferences for alkylation of a series of novel parasubstituted aniline mustards linked to the DNA-intercalating chromophore 9-aminoacridine by an alkyl chain of variable length were studied by using procedures analogous to Maxam-Gilbert reactions. The compounds alkylate DNA at both guanine and adenine sites. For mustards linked to the acridine by a short alkyl chain through a para O- or S-link group, 5'-GT sequences are the most preferred sites at which N7-guanine alkylation occurs. For analogues with longer chain lengths, the preference of 5'-GT sequences diminishes in favor of N7-adenine alkylation at the complementary 5'-AC sequence. Magnesium ions are shown to selectively inhibit alkylation at the N7 of adenine (in the major groove) by these compounds but not the alkylation at the N3 of adenine (in the minor groove) by the antitumor antibiotic CC-1065. Effects of chromophore variation were also studied by using aniline mustards linked to quinazoline and sterically hindered tert-butyl-9-aminoacridine chromophores. The results demonstrate that in this series of DNA-directed mustards the noncovalent interactions of the carrier chromophores with DNA significantly modify the sequence selectivity of alkylation by the mustard. Relationships between the DNA alkylation patterns of these compounds and their biological activities are discussed.

  9. Effects of alkyl parabens on plant pathogenic fungi.

    PubMed

    Ito, Shinsaku; Yazawa, Satoru; Nakagawa, Yasutaka; Sasaki, Yasuyuki; Yajima, Shunsuke

    2015-04-15

    Alkyl parabens are used as antimicrobial preservatives in cosmetics, food, and pharmaceutical products. However, the mode of action of these chemicals has not been assessed thoroughly. In this study, we determined the effects of alkyl parabens on plant pathogenic fungi. All the fungi tested, were susceptible to parabens. The effect of linear alkyl parabens on plant pathogenic fungi was related to the length of the alkyl chain. In addition, the antifungal activity was correlated with the paraben-induced inhibition of oxygen consumption. The antifungal activity of linear alkyl parabens likely originates, at least in part, from their ability to inhibit the membrane respiratory chain, especially mitochondrial complex II. Additionally, we determined that some alkyl parabens inhibit Alternaria brassicicola infection of cabbage.

  10. Alkylation damage by lipid electrophiles targets functional protein systems.

    PubMed

    Codreanu, Simona G; Ullery, Jody C; Zhu, Jing; Tallman, Keri A; Beavers, William N; Porter, Ned A; Marnett, Lawrence J; Zhang, Bing; Liebler, Daniel C

    2014-03-01

    Protein alkylation by reactive electrophiles contributes to chemical toxicities and oxidative stress, but the functional impact of alkylation damage across proteomes is poorly understood. We used Click chemistry and shotgun proteomics to profile the accumulation of proteome damage in human cells treated with lipid electrophile probes. Protein target profiles revealed three damage susceptibility classes, as well as proteins that were highly resistant to alkylation. Damage occurred selectively across functional protein interaction networks, with the most highly alkylation-susceptible proteins mapping to networks involved in cytoskeletal regulation. Proteins with lower damage susceptibility mapped to networks involved in protein synthesis and turnover and were alkylated only at electrophile concentrations that caused significant toxicity. Hierarchical susceptibility of proteome systems to alkylation may allow cells to survive sublethal damage while protecting critical cell functions.

  11. Method of using polysilane positive photoresist materials

    DOEpatents

    Harrah, L.A.; Zeigler, J.M.

    1986-05-06

    New polysilane copolymers comprise recurring units of --Si(X)(Y)-- and Si(A)(B)--, Si(X)(Y) being different from Si(A)(B), wherein X and Y together have 1-13 carbon atoms, and X and Y each independently is hydrogen, alkyl, cycloalkyl, phenyl, alkylphenyl, or phenylalkyl, with the proviso that only one of X and Y contains a phenyl moiety, or together X and Y are an alkylene group forming a ring with the adjoining Si atom, and wherein A and B together have 3-13 carbon atoms, and A and B each independently is alkyl or cycloalkyl, with the proviso (a) that when one of A and B is ethyl, the other is not methyl or ethyl, and (b) that when one of A ad B is n-propyl and the other is methyl, X and Y are not both methyl. Corresponding homopolysilanes are also provided. Upon ultraviolet irradiation, they photodepolymerize to form volatile products. As a result, they represent a new class of photoresists which enable direct formation of a positive image eliminating the heretofore required development step.

  12. Method of using polysilane positive photoresist materials

    DOEpatents

    Harrah, Larry A.; Zeigler, John M.

    1986-01-01

    New polysilane copolymers comprise recurring units of --Si(X)(Y)-- and Si(A)(B)--, Si(X)(Y) being different from Si(A)(B), wherein X and Y together have 1-13 carbon atoms, and X and Y each independently is hydrogen, alkyl, cycloalkyl, phenyl, alkylphenyl, or phenylalkyl, with the proviso that only one of X and Y contains a phenyl moiety, or together X and Y are an alkylene group forming a ring with the adjoining Si atom, and wherein A and B together have 3-13 carbon atoms, and A and B each independently is alkyl or cycloalkyl, with the proviso (a) that when one of A and B is ethyl, the other is not methyl or ethyl, and (b) that when one of A ad B is n-propyl and the other is methyl, X and Y are not both methyl. Corresponding homopolysilanes are also provided. Upon ultraviolet irradiation, they photodepolymerize to form volatile products. As a result, they represent a new class of photoresists which enable direct formation of a positive image eliminating the heretofore required development step.

  13. Polysilane positive photoresist materials and methods for their use

    DOEpatents

    Harrah, Larry A.; Zeigler, John M.

    1986-01-01

    New polysilane copolymers comprise recurring units of --Si(X)(Y)-- and Si(A)(B)--, Si(X)(Y) being different from Si(A)(B), wherein X and Y together have 1-13 carbon atoms, and X and Y each independently is hydrogen, alkyl, cycloalkyl, phenyl, alkylphenyl, or phenylalkyl, with the proviso that only one of X and Y contains a phenyl moiety, or together X and Y are an alkylene group forming a ring with the adjoining Si atom, and wherein A and B together have 3-13 carbon atoms, and A and B each independently is alkyl or cycloalkyl, with the proviso (a) that when one of A and B is ethyl, the other is not methyl or ethyl, and (b) that when one of A and B is n-propyl and the other is methyl, X and Y are not both methyl. Corresponding homopolysilanes are also provided. Upon ultraviolet irradiation, they photodepolymerize to form volatile products. As a result, they represent a new class of photoresists which enable direct formation of a positive image eliminating the heretofore required development step.

  14. Polysilane positive photoresist materials and methods for their use

    DOEpatents

    Harrah, L.A.; Zeigler, J.M.

    1984-04-05

    New polysilane copolymers comprise recurring units of -Si(X)(Y)- and Si(A)(B)-, Si(X)(Y) being different from Si(A)(B). X and Y together have 1 to 13 carbon atoms, and X and Y each independently is hydrogen, alkyl, cycloalkyl, phenyl, alkylphenyl, or phenylalkyl, with the proviso that only one of X and Y contains a phenyl moiety, or together X and Y are an alkylene group forming a ring with the adjoining Si atom. A and B together have 3 to 13 carbon atoms, and A and B each independently is alkyl or cycloalkyl, with the proviso that when one of A and B is ethyl, the other is not methyl or ethyl, and that when one of A and B is n-propyl and the other is methyl, X and Y are not both methyl. Corresponding homopolysilanes are also provided. Upon ultraviolet irradiation, they photodepolymerize to form volatile products. As a result, they represent a new class of photoresists which enable direct formation of a positive image eliminating the heretofore required development step.

  15. Lithium perchlorate-nitromethane-promoted alkylation of anilines with arylmethanols.

    PubMed

    Zhou, Jun; Mao, Hai-Feng; Wang, Lu; Zou, Jian-Ping; Zhang, Wei

    2011-11-01

    A new application of lithium perchlorate-nitromethane (LPNM) for the formation of aromatic C-N and C-C bonds is introduced. LPNM-promoted reactions of anilines with diarylmethanols selectively generate N-alkylated anilines or mono and double Friedel-Crafts alkylation products under different conditions by changing the reaction time, reaction temperature, and the ratio of the reactants. This method does not require the use of transition metal catalysts to prepare alkylated aniline derivatives.

  16. Corrosion abatement in sulfuric acid alkylation unit horizontal contactors

    SciTech Connect

    Schutt, H.U.

    1999-03-01

    A leak to the atmosphere in the hydraulic end cone of a horizontal contactor and the realization that basic corrosion data are not available for high-throughput process conditions in alkylation units prompted a laboratory study to develop the lacking expertise. Corrosion in the horizontal contractor of an alkylation unit was mitigated successfully by saturating fresh alkylation acid with ferrous sulfate (FeSO{sub 4}).

  17. Photochemical Production of Alkyl Nitrates in the Tropical Pacific Ocean

    NASA Astrophysics Data System (ADS)

    Dahl, E. E.; Yvon-Lewis, S. A.; Saltzman, E. S.

    2005-12-01

    Alkyl nitrates are important to the tropospheric NOx/ozone cycle because they represent a significant fraction of the reactive nitrogen (NOy). Previous work has shown that there is an oceanic source of alkyl nitrates. A photochemical mechanism for the formation of alkyl nitrates in seawater has been proposed. This mechanism involves the reaction of ROO and NO, where ROO is an alkyl peroxy radical. ROO and NO radicals in seawater are derived from the photolysis of DOM and nitrite, respectively. In this study, the photochemical production of low molecular weight alkyl nitrates (C1-C3) was observed in shipboard incubation experiments in the tropical Pacific during the PHASE 1 cruise. Seawater samples from several regions, including high and low-chlorophyll areas, were collected and incubated. Alkyl nitrate production rates as high as 2 nM/hour were observed. The production rate of alkyl nitrates was clearly dependent upon the initial concentration of nitrite, most likely as the source for NO radicals. While the magnitude of production varied between sample locations, the ratios of the production rates of the various alkyl nitrates remained relatively constant. The observed production ratios of methyl, ethyl, isopropyl, and n-propyl nitrate were 5.9:1.0:0.1:0.2. These ratios presumably reflect the speciation of peroxy radicals formed in seawater, and the yield of alkyl nitrates from the ROO+NO reaction. The observed production rate ratios are similar to the concentration ratios of alkyl nitrates observed in ambient seawater and the overlying atmosphere during the study. A comparison of the measured production rates and the observed concentrations, suggests that photochemically produced alkyl nitrates are a major source of atmospheric alkyl nitrates in the surface ocean and marine atmosphere.

  18. Alkyl Chlorides as Hydrogen Bond Acceptors

    SciTech Connect

    Nadas, Janos I; Vukovic, Sinisa; Hay, Benjamin

    2012-01-01

    To gain an understanding of the role of an alkyl chloride as a hydrogen bond acceptor, geometries and interaction energies were calculated at the MP2/aug-cc-pVDZ level of theory for complexes between ethyl chloride and representative hydrogen donor groups. The results establish that these donors, which include hydrogen cyanide, methanol, nitrobenzene, pyrrole, acetamide, and N-methylurea, form X-H {hor_ellipsis} Cl hydrogen bonds (X = C, N, O) of weak to moderate strength, with {Delta}E values ranging from -2.8 to -5.3 kcal/mol.

  19. Determination of reaction rate constants for alkylation of 4-(p-nitrobenzyl) pyridine by different alkylating agents.

    PubMed

    Walles, S A

    1980-02-01

    The rate constants have been determined for the reaction between some different alkylating agents and 4-(p-nitrobenzyl) pyridine (NBP) in methanol. These constants have been compared with those for alkylation of aniline in water. All the constants were lower in methanol than in water but in different degrees. The rate constants of the different alkylating agents have been calculated at a nucleophilic strength n=2. The genetic risk defined as the degree of alkylation of a nucleophile (n=2) is equivalent to the rate constant kn=2 and the target dose. The dependence of the genetic risk on the rate constant (kn=2) is discussed.

  20. 40 CFR 721.10218 - 2-Propenoic acid, 2-mehtyl-, C12-15-branched and linear alkyl esters, telomers with alkyl 2...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-branched and linear alkyl esters, telomers with alkyl 2- thio]-2-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated (generic). 721.10218 Section 721.10218...-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated...

  1. 40 CFR 721.10218 - 2-Propenoic acid, 2-mehtyl-, C12-15-branched and linear alkyl esters, telomers with alkyl 2...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-branched and linear alkyl esters, telomers with alkyl 2- thio]-2-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated (generic). 721.10218 Section 721.10218...-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated...

  2. 40 CFR 721.10218 - 2-Propenoic acid, 2-mehtyl-, C12-15-branched and linear alkyl esters, telomers with alkyl 2...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-branched and linear alkyl esters, telomers with alkyl 2- thio]-2-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated (generic). 721.10218 Section 721.10218...-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated...

  3. 40 CFR 721.10218 - 2-Propenoic acid, 2-mehtyl-, C12-15-branched and linear alkyl esters, telomers with alkyl 2...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-branched and linear alkyl esters, telomers with alkyl 2- thio]-2-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated (generic). 721.10218 Section 721.10218...-alkanoate, aminoalkyl methacrylate and alkyl methacrylate, tert-Bu 2-ethylhexanoperoxoate-initiated...

  4. Radioiodination of Aryl-Alkyl Cyclic Sulfates

    PubMed Central

    Mushti, Chandra; Papisov, Mikhail I.

    2015-01-01

    Among the currently available positron emitters suitable for Positron Emission Tomography (PET), 124I has the longest physical half-life (4.2 days). The long half-life and well-investigated behavior of iodine in vivo makes 124I very attractive for pharmacological studies. In this communication, we describe a simple yet effective method for the synthesis of novel 124I labeled compounds intended for PET imaging of arylsulfatase activity in vivo. Arylsulfatases have important biological functions, and genetic deficiencies of such functions require pharmacological replacement, the efficacy of which must be properly and non-invasively evaluated. These enzymes, even though their natural substrates are mostly of aliphatic nature, hydrolyze phenolic sulfates to phenol and sulfuric acid. The availability of [124I]iodinated substrates is expected to provide a PET-based method for measuring their activity in vivo. The currently available methods of synthesis of iodinated arylsulfates usually require either introducing of a protected sulfate ester early in the synthesis or introduction of sulfate group at the end of synthesis in a separate step. The described method gives the desired product in one step from an aryl-alkyl cyclic sulfate. When treated with iodide, the source cyclic sulfate opens with substitution of iodide at the alkyl center and gives the desired arylsulfate monoester. PMID:23135631

  5. Microstructure of Hydrophobically Modified Alkyl Acrylamide Hydrogels

    NASA Astrophysics Data System (ADS)

    Tian, Jun; Seery, Thomas A. P.; Ho, Derek L.; Weiss, R. A.

    2004-03-01

    Hydrophobically modified water-soluble acrylamide polymers have a variety of applications, including viscosity thickeners, microencapsulation, biosensors and controlled drug delivery systems. The microstructure of copolymer hydrogels of N,N-dimethylacrylamide (DMA) or N-isopropylacrylamide(NIPA) modified with 2-(N-ethylfluorooctanesulfonamido)ethyl acrylate, FOSA, was studied by small angle x-ray (SAXS) and neutron scattering (SANS). Swelling and DSC measurements showed that FOSA/NIPA gels exhibited a volume phase transition (VPT), but that FOSA/DMA gels did not. A modified interacting core-shell model was used to explain the SAXS and SANS data for both gels. The crosslink junctions of the gel consisted of nanophase-separated FOSA domains as the core surrounded by a water-poor layer of the alkyl acrylamide. These nanodomains were dispersed in a matrix of water-swollen alkyl acrylamide that had large scale heterogeneities. The average spherical core radius ranged from 1 to 3 nm and the average shell thickness ranged from 1 to 1.5 nm; the aggregation number ranged from 10 to 200.

  6. ESCHERICHIA COLI Gene Induction by Alkylation Treatment

    PubMed Central

    Volkert, Michael R.; Nguyen, Dinh C.; Beard, K. Christopher

    1986-01-01

    Searches for alkylation-inducible (aid) genes of Escherichia coli have been conducted by screening random fusions of the Mu-dl(ApR lac) phage for fusions showing increased β-galactosidase activity after treatment with methylating agents, but not after treatments with UV-irradiation. In this report we describe gene fusions that are specifically induced by alkylation treatments. Nine new mutants are described, and their properties are compared with the five mutants described previously. The total of 14 fusion mutants map at five distinct genetic loci. They can be further subdivided on the basis of their induction by methyl methanesulfonate (MMS) and N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). alkA, aidB and aidD are induced by both agents and appear to be regulated by ada. Neither aidC nor aidI is regulated by ada. Moreover, since aidC is induced only by MNNG and aidI is induced only by MMS, these two genes are likely to be individually regulated. Thus, there appear to be at least three different regulatory mechanisms controlling aid genes. PMID:3080354

  7. Escherichia coli gene induction by alkylation treatment.

    PubMed

    Volkert, M R; Nguyen, D C; Beard, K C

    1986-01-01

    Searches for alkylation-inducible (aid) genes of Escherichia coli have been conducted by screening random fusions of the Mu-dl(ApR lac) phage for fusions showing increased beta-galactosidase activity after treatment with methylating agents, but not after treatments with UV-irradiation. In this report we describe gene fusions that are specifically induced by alkylation treatments. Nine new mutants are described, and their properties are compared with the five mutants described previously. The total of 14 fusion mutants map at five distinct genetic loci. They can be further subdivided on the basis of their induction by methyl methanesulfonate (MMS) and N-methyl-N' -nitro-N-nitrosoguanidine (MNNG). alkA, aidB and aidD are induced by both agents and appear to be regulated by ada. Neither aidC nor aidI is regulated by ada. Moreover, since aidC is induced only by MNNG and aidI is induced only by MMS, these two genes are likely to be individually regulated. Thus, there appear to be at least three different regulatory mechanisms controlling aid genes.

  8. Partial Crystallinity in Alkyl Side Chain Polymers.

    NASA Astrophysics Data System (ADS)

    Sahni, Vasav; Prasad, Shishir; Villate, Johanna; Jiang, Zhang; Sinha, Sunil; Dhinojwala, Ali

    2009-03-01

    Surface freezing is the formation of a crystalline monolayer at the free surface of a melt at a temperature Ts, a few degrees above the bulk freezing temperature, Tb. This effect, i.e. Ts> Tb, common to many chain molecules, is in marked contrast with the surface melting effect, i.e. Ts<=Tb, shown by almost all other materials. Various theoretical and experimental studies have been done to characterize the monolayer formed when the surface freezes before the bulk. We have studied the structure of a novel crystalline surface monolayer on top of a disordered melt of the same material (poly(n-alkyl acrylate)s) using grazing incidence x-ray diffraction. The grazing incidence x-ray diffraction, surface tension, and bulk latent heat results show that there is partial side-chain crystallinity. Also, the surface tension results explain the trend of the difference between the surface order-to-disorder transition temperature and the bulk melting temperature (δT) as a function of side chain length. The behavior of the crystal length, crystal spacing and tilt with varying alkyl chain length and temperature was also studied.

  9. The photodissociation dynamics of alkyl radicals

    SciTech Connect

    Giegerich, Jens; Fischer, Ingo

    2015-01-28

    The photodisscociation dynamics of the alkyl radicals i-propyl (CH(CH{sub 3}){sub 2}) and t-butyl (C(CH{sub 3}){sub 3}) are investigated by H-atom photofragment imaging. While i-propyl is excited at 250 nm, the photodynamics of t-butyl are explored over a large energy range using excitation wavelengths between 347 nm and 233 nm. The results are compared to those obtained previously for ethyl, CH{sub 3}CH{sub 2}, and to those reported for t-butyl using 248 nm excitation. The translational energy (E{sub T}) distribution of the H-atom photofragments is bimodal and appears rather similar for all three radicals. The low E{sub T} part of the distribution shows an isotropic photofragment angular distribution, while the high E{sub T} part is associated with a considerable anisotropy. Thus, for t-butyl, two H-atom loss channels of roughly equal importance have been identified in addition to the CH{sub 3}-loss channel reported previously. A mechanism for the photodissociation of alkyl radicals is suggested that is based on interactions between Rydberg- and valence states.

  10. Effect of surfactant alkyl chain length on soil cadmium desorption using surfactant/ligand systems.

    PubMed

    Shin, Mari; Barrington, Suzelle F; Marshall, William D; Kim, Jin-Woo

    2005-02-01

    The effect of surfactant alkyl chain length on soil Cd desorption was studied using nonionic surfactants of polyethylene oxide (PEO) of PEO chain lengths of 7.5 (Triton X-114), 9.5 (Triton X-100), 30 (Triton X-305), or 40 units (Triton X-405) in combination with the I- ligand. Triplicate 1 g soil samples were equilibrated with 15 ml of surfactant-ligand mixture, at concentrations of 0.025, 0.50 or 0.10, and 0.0, 0.168 or 0.336 mol/l, respectively. After shaking the samples for 24 h, the supernatant fraction was analyzed for Cd content to determine the percent of Cd desorbed from the soil. After five successive washings, 53%, 40% and 25% of Cd had been desorbed by 0.025, 0.050 or 0.10 mol/l of Triton X-114, respectively, in the presence of 0.336 mol/l of I-, whereas with the same conditions, Triton X-100 desorbed 61%, 57% and 56% Cd and either Triton X-305 or Triton X-405 desorbed 51, 40 and 14 to 16% Cd. The most efficient Cd desorption was obtained using 0.025 mol/l Triton X-100 in admixture with 0.336 mol/l I-. Increased surfactant concentration was detrimental to Cd desorption consistent with a process that blocked ligand access to the soil particle surface. After 5 washings,the cumulative cadmium desorption decreased with increasing surfactant alkyl chain length, indicating that the metal-ligand complexes are preferably stabilized by the micelles' hydrophobic octyl phenyl (OP) group rather than by the hydrophilic PEO group. In the absence of ligand, the surfactants alone desorbed less than 1% Cd from the contaminated soil, suggesting that the ligand, rather than the surfactant, extracts the metal, to be subsequently stabilized within the surfactant micelles.

  11. 40 CFR 721.6070 - Alkyl phosphonate ammonium salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkyl phosphonate ammonium salts. 721... Substances § 721.6070 Alkyl phosphonate ammonium salts. (a) Chemical substances and significant new uses... salts (PMNs P-93-725 and P-93-726) are subject to reporting under this section for the significant...

  12. 40 CFR 721.6070 - Alkyl phosphonate ammonium salts.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl phosphonate ammonium salts. 721... Substances § 721.6070 Alkyl phosphonate ammonium salts. (a) Chemical substances and significant new uses... salts (PMNs P-93-725 and P-93-726) are subject to reporting under this section for the significant...

  13. 40 CFR 721.2155 - Alkoxyamino-alkyl-coumarin (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkoxyamino-alkyl-coumarin (generic... Substances § 721.2155 Alkoxyamino-alkyl-coumarin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  14. 40 CFR 721.2155 - Alkoxyamino-alkyl-coumarin (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkoxyamino-alkyl-coumarin (generic... Substances § 721.2155 Alkoxyamino-alkyl-coumarin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  15. 40 CFR 721.2155 - Alkoxyamino-alkyl-coumarin (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkoxyamino-alkyl-coumarin (generic... Substances § 721.2155 Alkoxyamino-alkyl-coumarin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  16. 40 CFR 721.2155 - Alkoxyamino-alkyl-coumarin (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkoxyamino-alkyl-coumarin (generic... Substances § 721.2155 Alkoxyamino-alkyl-coumarin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  17. 40 CFR 721.2155 - Alkoxyamino-alkyl-coumarin (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkoxyamino-alkyl-coumarin (generic... Substances § 721.2155 Alkoxyamino-alkyl-coumarin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  18. 40 CFR 721.10317 - Alkyl phosphate derivative (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl phosphate derivative (generic... Specific Chemical Substances § 721.10317 Alkyl phosphate derivative (generic). (a) Chemical substance and... phosphate derivative (PMN P-02-1040) is subject to reporting under this section for the significant new...

  19. 40 CFR 721.10317 - Alkyl phosphate derivative (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl phosphate derivative (generic... Specific Chemical Substances § 721.10317 Alkyl phosphate derivative (generic). (a) Chemical substance and... phosphate derivative (PMN P-02-1040) is subject to reporting under this section for the significant new...

  20. 40 CFR 721.10317 - Alkyl phosphate derivative (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl phosphate derivative (generic... Specific Chemical Substances § 721.10317 Alkyl phosphate derivative (generic). (a) Chemical substance and... phosphate derivative (PMN P-02-1040) is subject to reporting under this section for the significant new...

  1. Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.

    PubMed

    Chen, Wei; Du, Wei; Yue, Lei; Li, Rui; Wu, Yong; Ding, Li-Sheng; Chen, Ying-Chun

    2007-03-07

    The C3-selective enantioselective Michael-type Friedel-Crafts alkylations of indoles with nonchelating alpha,beta-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to -20 degrees C. Moderate to good ee (47-89%) has been achieved.

  2. An overview of the properties of fatty acid alkyl esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Fatty acid alkyl esters of plant oils, especially in the form of methyl esters, have numerous applications with fuel use having received the most attention in recent times due to the potential high volume. Various properties imparted by neat fatty acid alkyl esters have been shown to influence fuel ...

  3. 40 CFR 721.840 - Alkyl substituted diaromatic hydrocarbons.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... hydrocarbons. 721.840 Section 721.840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.840 Alkyl substituted diaromatic hydrocarbons. (a) Chemical substance... alkyl substituted di-aro-matic hydrocarbons (PMN P-91-710) is subject to reporting under this...

  4. 40 CFR 721.840 - Alkyl substituted diaromatic hydrocarbons.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... hydrocarbons. 721.840 Section 721.840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.840 Alkyl substituted diaromatic hydrocarbons. (a) Chemical substance... alkyl substituted di-aro-matic hydrocarbons (PMN P-91-710) is subject to reporting under this...

  5. 40 CFR 721.840 - Alkyl substituted diaromatic hydrocarbons.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... hydrocarbons. 721.840 Section 721.840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.840 Alkyl substituted diaromatic hydrocarbons. (a) Chemical substance... alkyl substituted di-aro-matic hydrocarbons (PMN P-91-710) is subject to reporting under this...

  6. 40 CFR 721.840 - Alkyl substituted diaromatic hydrocarbons.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... hydrocarbons. 721.840 Section 721.840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.840 Alkyl substituted diaromatic hydrocarbons. (a) Chemical substance... alkyl substituted di-aro-matic hydrocarbons (PMN P-91-710) is subject to reporting under this...

  7. 40 CFR 721.840 - Alkyl substituted diaromatic hydrocarbons.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... hydrocarbons. 721.840 Section 721.840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.840 Alkyl substituted diaromatic hydrocarbons. (a) Chemical substance... alkyl substituted di-aro-matic hydrocarbons (PMN P-91-710) is subject to reporting under this...

  8. 40 CFR 721.10073 - Modified alkyl acrylamide (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Modified alkyl acrylamide (generic... Specific Chemical Substances § 721.10073 Modified alkyl acrylamide (generic). (a) Chemical substance and... acrylamide (PMN P-05-536) is subject to reporting under this section for the significant new uses...

  9. 40 CFR 721.10073 - Modified alkyl acrylamide (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Modified alkyl acrylamide (generic... Specific Chemical Substances § 721.10073 Modified alkyl acrylamide (generic). (a) Chemical substance and... acrylamide (PMN P-05-536) is subject to reporting under this section for the significant new uses...

  10. 40 CFR 721.10073 - Modified alkyl acrylamide (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Modified alkyl acrylamide (generic... Specific Chemical Substances § 721.10073 Modified alkyl acrylamide (generic). (a) Chemical substance and... acrylamide (PMN P-05-536) is subject to reporting under this section for the significant new uses...

  11. 40 CFR 721.10073 - Modified alkyl acrylamide (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Modified alkyl acrylamide (generic... Specific Chemical Substances § 721.10073 Modified alkyl acrylamide (generic). (a) Chemical substance and... acrylamide (PMN P-05-536) is subject to reporting under this section for the significant new uses...

  12. 40 CFR 721.10073 - Modified alkyl acrylamide (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Modified alkyl acrylamide (generic... Specific Chemical Substances § 721.10073 Modified alkyl acrylamide (generic). (a) Chemical substance and... acrylamide (PMN P-05-536) is subject to reporting under this section for the significant new uses...

  13. 40 CFR 721.6070 - Alkyl phosphonate ammonium salts.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl phosphonate ammonium salts. 721... Substances § 721.6070 Alkyl phosphonate ammonium salts. (a) Chemical substances and significant new uses... salts (PMNs P-93-725 and P-93-726) are subject to reporting under this section for the significant...

  14. 40 CFR 721.6070 - Alkyl phosphonate ammonium salts.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl phosphonate ammonium salts. 721... Substances § 721.6070 Alkyl phosphonate ammonium salts. (a) Chemical substances and significant new uses... salts (PMNs P-93-725 and P-93-726) are subject to reporting under this section for the significant...

  15. 40 CFR 721.6070 - Alkyl phosphonate ammonium salts.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl phosphonate ammonium salts. 721... Substances § 721.6070 Alkyl phosphonate ammonium salts. (a) Chemical substances and significant new uses... salts (PMNs P-93-725 and P-93-726) are subject to reporting under this section for the significant...

  16. 40 CFR 721.10430 - Tetra alkyl ammonium salt (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Tetra alkyl ammonium salt (generic... Specific Chemical Substances § 721.10430 Tetra alkyl ammonium salt (generic). (a) Chemical substance and... ammonium salt (PMN P-97-823) is subject to reporting under this section for the significant new...

  17. 40 CFR 721.10430 - Tetra alkyl ammonium salt (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Tetra alkyl ammonium salt (generic... Specific Chemical Substances § 721.10430 Tetra alkyl ammonium salt (generic). (a) Chemical substance and... ammonium salt (PMN P-97-823) is subject to reporting under this section for the significant new...

  18. Degradable Polymer Composites Fabricated from Starch and Alkyl Cyanoacrylate Monomer

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Degradable polymer composites are fabricated from alkyl cyanoacrylate monomer and starch without special equipment. Alkyl cyanoacrylate, which is a major component of “super glue”, is a monomer that polymerizes at room temperature in the presence of initiators. During the fabrication of polymer com...

  19. Deaminative and decarboxylative catalytic alkylation of amino acids with ketones.

    PubMed

    Kalutharage, Nishantha; Yi, Chae S

    2013-12-16

    It cuts two ways: The cationic [Ru-H] complex catalyzes selective coupling of α- and β-amino acids with ketones to form α-alkylated ketone products. The reaction involves CC and CN bond cleavage which result in regio- and stereoselective alkylation using amino acids. A broad substrate scope and high functional-group tolerance is demonstrated.

  20. Direct, Regioselective N-Alkylation of 1,3-Azoles.

    PubMed

    Chen, Shuai; Graceffa, Russell F; Boezio, Alessandro A

    2016-01-04

    Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.

  1. 40 CFR 721.10677 - Alkyl phosphonate (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10677 Alkyl phosphonate (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as alkyl phosphonate (PMN...

  2. 40 CFR 721.10711 - Alkyl substituted catechol (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl substituted catechol (generic... Specific Chemical Substances § 721.10711 Alkyl substituted catechol (generic). (a) Chemical substance and... substituted catechol (PMN P-13-197) is subject to reporting under this section for the significant new...

  3. 40 CFR 721.655 - Ethoxylated alkyl quaternary ammonium compound.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... compound. 721.655 Section 721.655 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.655 Ethoxylated alkyl quaternary ammonium compound. (a) Chemical... as an ethoxylated alkyl quaternary ammonium compound (PMN P-96-573) is subject to reporting...

  4. 40 CFR 721.655 - Ethoxylated alkyl quaternary ammonium compound.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... compound. 721.655 Section 721.655 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.655 Ethoxylated alkyl quaternary ammonium compound. (a) Chemical... as an ethoxylated alkyl quaternary ammonium compound (PMN P-96-573) is subject to reporting...

  5. 40 CFR 721.655 - Ethoxylated alkyl quaternary ammonium compound.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... compound. 721.655 Section 721.655 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.655 Ethoxylated alkyl quaternary ammonium compound. (a) Chemical... as an ethoxylated alkyl quaternary ammonium compound (PMN P-96-573) is subject to reporting...

  6. 40 CFR 721.655 - Ethoxylated alkyl quaternary ammonium compound.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... compound. 721.655 Section 721.655 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.655 Ethoxylated alkyl quaternary ammonium compound. (a) Chemical... as an ethoxylated alkyl quaternary ammonium compound (PMN P-96-573) is subject to reporting...

  7. 40 CFR 721.655 - Ethoxylated alkyl quaternary ammonium compound.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... compound. 721.655 Section 721.655 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.655 Ethoxylated alkyl quaternary ammonium compound. (a) Chemical... as an ethoxylated alkyl quaternary ammonium compound (PMN P-96-573) is subject to reporting...

  8. Optimization of alkylating agent prodrugs derived from phenol and aniline mustards: a new clinical candidate prodrug (ZD2767) for antibody-directed enzyme prodrug therapy (ADEPT).

    PubMed

    Springer, C J; Dowell, R; Burke, P J; Hadley, E; Davis, D H; Blakey, D C; Melton, R G; Niculescu-Duvaz, I

    1995-12-22

    Sixteen novel potential prodrugs derived from phenol or aniline mustards and their 16 corresponding drugs with ring substitution and/or different alkylating functionalities were designed. The [[[4-]bis(2-bromoethyl)-(1a), [[[4-[bis(2-iodoethyl)-(1b), and [[[4-[(2-chloroethyl)-[2-(mesyloxy)ethyl]amino]phenyl]oxy] carbonyl]-L-glutamic acids (1c), their [[[2- and 3-substituted-4-[bis(2-chloroethyl)amino]phenyl]oxy]carbonyl]-L- glutamic acids (1e-1), and the [[3-substituted-4-[bis(2-chloroethyl)amino]phenyl]carbamoyl]-L- glutamic acids (1o-r) were synthesized. They are bifunctional alkylating agents in which the activating effect of the phenolic hydroxyl or amino function is masked through an oxycarbonyl or a carbamoyl bond to a glutamic acid. These prodrugs were designed to be activated to their corresponding phenol and aniline nitrogen mustard drugs at a tumor site by prior administration of a monoclonal antibody conjugated to the bacterial enzyme carboxypeptidase G2 (CPG2) in antibody-directed enzyme prodrug therapy (ADEPT). The synthesis of the analogous novel parent drugs (2a-r) is also described. The viability of a colorectal cell line (LoVo) was monitored with the potential prodrugs and the parent drugs. The differential in the cytotoxicity between the potential prodrugs and their corresponding active drugs ranged between 12 and > 195 fold. Compounds 1b-d,f,o exhibited substantial prodrug activity, since a cytotoxicity differential of > 100 was achieved compared to 2b-d,f,o respectively. The ability of the potential prodrugs to act as substrates for CPG2 was determined (kinetic parameters KM and kcat), and the chemical stability was measured for all the compounds. The unsubstituted phenols with different alkylating functionalities (1a-c) proved to have the highest ratio of the substrates kcat:KM. From these studies [[[4-[bis(2-iodoethyl)amino]phenyl]oxy]carbonyl]-L-glutamic acid (1b) emerges as a new ADEPT clinical trial candidate due to its physicochemical and

  9. Low-band-gap conjugated polymers of dithieno[2,3-b:7,6-b]carbazole and diketopyrrolopyrrole: effect of the alkyl side chain on photovoltaic properties.

    PubMed

    Deng, Yunfeng; Chen, Yagang; Liu, Jian; Liu, Lihui; Tian, Hongkun; Xie, Zhiyuan; Geng, Yanhou; Wang, Fosong

    2013-06-26

    Four donor–acceptor (D–A) conjugated polymers of dithieno[2,3-b;7,6-b]carbazole (DTC) and diketopyrrolopyrrole, which have different alkyls on the nitrogen atom in the DTC unit and are named as P-C8C8, P-C5C5, P-C12, and P-C10, respectively, have been synthesized for studying the effect of the alkyl side chains on the optoelectronic properties of the polymers. All polymers are soluble in various organic solvents and exhibit identical optical band gaps (E(g)(opt)) of ~1.3 eV and highest occupied molecular orbital energy levels of ~−5.1 eV. Organic thin-film transistors and bulk heterojunction polymer solar cells (BHJ PSCs) with phenyl-C(71)-butyric acid methyl ester (PC(71)BM) as the electron-accepting material were fabricated via solution spin-casting. Compared to the polymers substituted by branched alkyl chains, the polymers with straight alkyl chains show higher hole mobility. Of these polymers, P-C10 exhibits the highest field effect mobility up to 0.011 cm(2)/V·s. The alkyl chain on the DTC unit has a strong impact on the film morphology of polymer:PC(71)BM blends. Severe phase separation was found for polymers containing branched alkyl chains, and those with straight alkyl chains formed uniform films featuring fine phase separation. An open-circuit voltage (V(oc)) of 0.72 V, a short-circuit current density (J(sc)) of 13.4 mA/cm(2), a fill factor (FF) of 62%, and a power conversion efficiency (PCE) of 5.9% were demonstrated for BHJ PSCs based on the P-C10:PC(71)BM [1:3 (w/w)] blend film.

  10. Polyimide characterization studies - Effect of pendant alkyl groups

    NASA Technical Reports Server (NTRS)

    Jensen, B. J.; Young, P. R.

    1984-01-01

    The effect on selected polyimide properties when pendant alkyl groups were attached to the polymer backbone was investigated. A series of polymers were prepared using benzophenone tetracarboxylic acid dianhydride (BTDA) and seven different p-alkyl-m,p'-diaminobenzophenone monomers. The alkyl groups varied in length from C(1) (methyl) to C(9) (nonyl). The polyimide prepared from BTDA and m,p'-diaminobenzophenone was included as a control. All polymers were characterized by various chromatographic, spectroscopic, thermal, and mechanical techniques. Increasing the length of the pendant alkyl group resulted in a systematic decrease in glass transition temperature (Tg) for vacuum cured films. A 70 C decrease in Tg to 193 C was observed for the nonyl polymer compared to the Tg for the control. A corresponding systematic increase in Tg indicative of crosslinking, was observed for air cured films. Thermogravimetric analysis revealed a slight sacrifice in thermal stability with increasing alkyl length. No improvement in film toughness was observed.

  11. Determination of relative acidities of some alpha, omega-bis(3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl) alkanes.

    PubMed

    Karaböcek, S; Dalman, O; Nohut, S; Tüfekçi, M; Sancak, K; Güner, S

    1998-07-01

    The solutions of nine alpha, omega-bis(3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl) alkanes were titrated with tetrabutylammoniumhydroxide (TBAH) in methanol, using potentiometric methods. The half neutralization potentials values were found for all cases. Potentiometric titration curves of compounds in methanol with 0.03 M TBAH are similar to those of weak acids obtained in aqueous media with strong bases. Methanol is found to be a suitable medium for the weakly acidic compounds titrated since they are poorly dissolved in other organic solvents. A comparison among the compounds having the same alkyl chains between the two ring systems has shown that basicity increases and acidity decreases as the size of alkyl chains increases. However, the compound with a substituted phenyl group was found to be the most acidic one among the examined compounds indicating that phenyl group donates ring electrons less effectively to the system. This can be attributed to the stability of the benzene ring.

  12. Alkylation of terminal alkynes with transient σ-alkylpalladium(II) complexes: a carboalkynylation route to alkyl-substituted alkynes.

    PubMed

    Zhou, Ming-Bo; Huang, Xiao-Cheng; Liu, Yan-Yun; Song, Ren-Jie; Li, Jin-Heng

    2014-02-10

    A mild and general alkylation of terminal alkynes with transient σ-alkylpalladium(II) complexes for assembling alkyl-substituted alkynes is described. This method represents a new way to the use of transient σ-alkylpalladium(II) complexes in organic synthesis through 1,2-carboalkynylation of alkenes.

  13. Cu(I)-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with 2-Aryl-N-sulfonylaziridines as Alkylating Agents.

    PubMed

    Ge, Chen; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia

    2016-07-01

    A highly enantioselective Friedel-Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu(CH3CN)4BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process.

  14. Iron-Catalyzed Cross-Coupling of Unactivated, Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents

    PubMed Central

    Denmark, Scott E.; Cresswell, Alexander J.

    2013-01-01

    The first systematic investigation of unactivated aliphatic sulfur compounds as electrophiles in transition metal-catalyzed cross-coupling are described. Initial studies focused on discerning the structural and electronic features of the organosulfur substrate which enable the challenging oxidative addition to the C(sp3)–S bond. Through extensive optimization efforts, an Fe(acac)3-catalyzed cross-coupling of unactivated alkyl aryl thio ethers with aryl Grignard reagents was realized, in which a nitrogen “directing group” on the S-aryl moiety of the thio ether served a critical role in facilitating the oxidative addition step. In addition, alkyl phenyl sulfones were found to be effective electrophiles in the Fe(acac)3-catalyzed cross-coupling with aryl Grignard reagents. For the latter class of electrophile, a thorough assessment of the various reaction parameters revealed a dramatic enhancement in reaction efficiency with an excess of TMEDA (8.0 equiv). The optimized reaction protocol was used to evaluate the scope of the method with respect to both the organomagnesium nucleophile and sulfone electrophile. PMID:24256193

  15. Synthesis and crystal structures of 7-bromo-5-(2‧-chloro)phenyl-3-hydroxy-1-methyl-1,2-dihydro-3H-1,4-benzodiazepin-2-one and 7-bromo-5-(2‧-chloro)phenyl-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepin-2,3-dione

    NASA Astrophysics Data System (ADS)

    Kravtsov, Victor Ch.; Fonari, Marina S.; Gdaniec, Мaria; Pavlovsky, Victor I.; Andronati, Sergei A.; Semenishyna, Ekaterina A.

    2012-06-01

    Treatment of 7-bromo-5-(2'-chloro)phenyl-3-hydroxy-1,2-dihydro-3H-1,4-benzodiazepin-2-one (1) with methyl or hexyl tosylate resulted in 7-bromo-5-(2'-chloro)phenyl-3-hydroxy-1-methyl-1,2-dihydro-3H-1,4-benzodiazepin-2-one (2) and 7-bromo-5-(2'-chloro)phenyl-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepin-2,3-dione (3). As confirmed by X-ray crystallography, the two products differ not only in the identity of the alkyl substituent in position 1 of the benzodiazepine fragment but also crystallize in different molecular forms resulting from proton migration. This alteration of the molecular structure leads to a significant change in the conformation of the central molecular fragment and influences the assembly mode in the crystal. In 3, centrosymmetric dimers formed via a pair of Nsbnd H⋯O hydrogen bonds are further linked into chains via Csbnd Br⋯Odbnd C halogen bond interaction. In turn in 2 there are two symmetry independent molecules, each giving a different set of intermolecular interactions. One of the molecules forms a dimer via Osbnd H⋯O interactions whereas the second one generates chain via Csbnd Br⋯Odbnd C halogen bond that is also assisted by a weak Osbnd H⋯Br hydrogen bond.

  16. Materials performance in HF-alkylation units

    SciTech Connect

    Forsen, O.; Aromaa, J.; Somervuori, M.; Tavi, M.

    1995-11-01

    Materials selection in HF-alkylation units is mostly based on long time experience. The most widely used material in the Station units is standard carbon steel, because it is capable to form a thick protective FeF{sub 2} layer in concentrated or anhydrous hydrofluoric acid. The corrosion resistance decreases, when the acid is dilute (less than 64% HF) or the temperature is above 160F (70 C). The composition and metallurgical state are also suspected to affect the corrosion resistance of carbon steel. The effect of composition appears more complicated than believed, especially the A-106 specification on the total amount of Cr+Ni+Cu+Mo+V < 1% should be studied more closely from the corrosion point of view. Laboratory tests showed that the uniform corrosion rate may be 100 times higher in galvanic contact of two dissimilar steels. The effect of galvanic contacts can neither be excluded in the process equipment corrosion cases.

  17. Bis(4-(3,4-dimethylenepyrrolidyl)-phenyl) methane

    NASA Technical Reports Server (NTRS)

    Ottenbrite, Raphael M. (Inventor)

    1989-01-01

    It is the primary object of the present invention to prepare high temperature polymeric materials, especially linear aromatic polyimides, which maintain their integrity and toughness during long exposure times at elevated temperatures. According to the present invention, this object is achieved, and the attending benefits are obtained, by first providing the bis(exocyclodiene) bis(4-(3,4-dinethylene pyrrolidyl) phenyl) methane, which is formed from the monomer N-phenyl 3,4-dimethylene pyrrolidine. This bis-(exocyclodiene) undergoes Diels-Alder reaction with a bismaleimide without the evolution of gaseous by-products, to form the aromatic polyimide.

  18. Investigation of double bond conversion, mechanical properties, and antibacterial activity of dental resins with different alkyl chain length quaternary ammonium methacrylate monomers (QAM).

    PubMed

    He, Jingwei; Söderling, Eva; Vallittu, Pekka K; Lassila, Lippo V J

    2013-01-01

    In order to endow dental resin with antibacterial activity, a series of antibacterial quaternary ammonium methacrylate monomers (QAM) with different substituted alkyl chain length (from 10 to 18) were incorporated into commonly used 2,2-bis[4-(2'-hydroxy-3'-methacryloyloxy-propoxy)-phenyl]propane (Bis-GMA)/triethyleneglycol dimethacrylate (TEGDMA) (50 wt/50 wt) dental resin as immobilized antibacterial agents. Double bond conversion (DC), flexural strength (FS) and modulus (FM), and young and mature biofilms inhibition effectiveness of prepared dental resins were studied and Bis-GMA/TEGDMA without QAM was used as reference. Results showed that there was no significant difference on DC, FS, and FM between copolymer with and without 5 wt% QAM. Substituted alkyl chain length of QAM had no influence on DC, FS, and FM of copolymer, but had influence on antibacterial activity of copolymer. Antibacterial activity of copolymer increased with increasing of substituted alkyl chain length of QAM, and the sequence followed as 5%C10 < 5%C11 ≈ 5%C12 < 5%C16 ≈ 5%C18. Copolymers containing C18 and C16 had the best inhibition effectiveness on both young biofilm and mature biofilm, copolymers containing C12 and C11 only had inhibition effectiveness on young biofilm and copolymer containing C10 had none inhibition effectiveness on neither young biofilm nor mature biofilm.

  19. Influence of alkyl chain length on the surface activity of antibacterial polymers derived from ROMP.

    PubMed

    Altay, Esra; Yapaöz, Melda Altıkatoğlu; Keskin, Bahadır; Yucesan, Gundoğ; Eren, Tarik

    2015-03-01

    The purpose of this study is to understand the antibacterial properties of cationic polymers on solid surfaces by investigating the structure-activity relationships. The polymer synthesis was carried via ring opening metathesis polymerization (ROMP) of oxanorbornene derivatives. Modulation of molecular weights and alkyl chain lengths of the polymers were studied to investigate the antibacterial properties on the glass surface. Fluorescein (Na salt) staining contact angle measurements were used to characterize the positive charge density and hydrophobicity on the polymer coated surfaces. Positive charge density for the surface coated polymers with molecular weights of 3000 and 10,000 g mol(-1) is observed to be in the range of 2.3-28.5 nmol cm(-2). The ROMP based cationic pyridinium polymer with hexyl unit exhibited the highest bactericidal efficiency against Escherichia coli on solid surface killing 99% of the bacteria in 5 min. However, phenyl and octyl functionalized quaternary pyridinium groups exhibited lower biocidal properties on the solid surfaces compared to their solution phase biocidal properties. Studying the effect of threshold polymer concentrations on the antibacterial properties indicated that changing the concentrations of polymer coatings on the solid surface dramatically influences antibacterial efficiency.

  20. Alkylating potential of styrene oxide: reactions and factors involved in the alkylation process.

    PubMed

    González-Pérez, Marina; Gómez-Bombarelli, Rafael; Pérez-Prior, M Teresa; Arenas-Valgañón, Jorge; García-Santos, M Pilar; Calle, Emilio; Casado, Julio

    2014-10-20

    The chemical reactivity of styrene-7,8-oxide (SO), an alkylating agent with high affinity for the guanine–N7 position and a probable carcinogen for humans, with 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to those of DNA bases, was investigated kinetically in water/dioxane media. UV–vis spectrophotometry and ultrafast liquid chromatography were used to monitor the reactions involved. It was found that in the alkylation process four reactions occur simultaneously: (a) the formation of a β-NBP–SO adduct through an SN2 mechanism; (b) the acid-catalyzed formation of the stable α-NBP–SO adduct through an SN2′ mechanism; (c) the base-catalyzed hydrolysis of the β-adduct, and (d) the acid-catalyzed hydrolysis of SO. At 37.5 °C and pH = 7.0 (in 7:3 water/dioxane medium), the values of the respective reaction rate constants were as follows: kalkβ = (2.1 ± 0.3) × 10–4 M–1 s–1, kalkα = (1.0 ± 0.1) × 10–4 M–1 s–1, khydAD = (3.06 ± 0.09) × 10–6 s–1, and khyd = (4.2 ± 0.9) × 10–6 s–1. These values show that, in order to determine the alkylating potential of SO, none of the four reactions involved can be neglected. Temperature and pH were found to exert a strong influence on the values of some parameters that may be useful to investigate possible chemicobiological correlations (e.g., in the pH 5.81–7.69 range, the fraction of total adducts formed increased from 24% to 90% of the initial SO, whereas the adduct lifetime of the unstable β-adduct, which gives an idea of the permanence of the adduct over time, decreased from 32358 to 13313 min). A consequence of these results is that the conclusions drawn in studies addressing alkylation reactions at temperatures and/or pH far from those of biological conditions should be considered with some reserve.

  1. 40 CFR 721.9825 - Phenyl substituted triazolinones.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... in combination with a chemical-resistant glove that has been demonstrated (EPA review not required... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.9825 Phenyl substituted triazolinones. (a) Chemical substance and significant new...

  2. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  3. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  4. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  5. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  6. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  7. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  8. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  9. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  10. Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same

    SciTech Connect

    Liston, T.V.

    1986-12-16

    A composition is described comprising a complex prepared by reacting a borated alkyl catechol and an oil soluble alkyl or alkenyl succinimide wherein the weight percent ratio of the alkyl or alkenyl succinimide to the borated alkyl catechol ranges from 3:1 to 16:1.

  11. Alkaline phosphatase revisited: hydrolysis of alkyl phosphates.

    PubMed

    O'Brien, Patrick J; Herschlag, Daniel

    2002-03-05

    Escherichia coli alkaline phosphatase (AP) is the prototypical two metal ion catalyst with two divalent zinc ions bound approximately 4 A apart in the active site. Studies spanning half a century have elucidated many structural and mechanistic features of this enzyme, rendering it an attractive model for investigating the potent catalytic power of bimetallic centers. Unfortunately, fundamental mechanistic features have been obscured by limitations with the standard assays. These assays generate concentrations of inorganic phosphate (P(i)) in excess of its inhibition constant (K(i) approximately 1 muM). This tight binding by P(i) has affected the majority of published kinetic constants. Furthermore, binding limits k(cat)/K(m) for reaction of p-nitrophenyl phosphate, the most commonly employed substrate. We describe a sensitive (32)P-based assay for hydrolysis of alkyl phosphates that avoids the complication of product inhibition. We have revisited basic mechanistic features of AP with these alkyl phosphate substrates. The results suggest that the chemical step for phosphorylation of the enzyme limits k(cat)/K(m). The pH-rate profile and additional results suggest that the serine nucleophile is active in its anionic form and has a pK(a) of < or = 5.5 in the free enzyme. An inactivating pK(a) of 8.0 is observed for binding of both substrates and inhibitors, and we suggest that this corresponds to ionization of a zinc-coordinated water molecule. Counter to previous suggestions, inorganic phosphate dianion appears to bind to the highly charged AP active site at least as strongly as the trianion. The dependence of k(cat)/K(m) on the pK(a) of the leaving group follows a Brønsted correlation with a slope of beta(lg) = -0.85 +/- 0.1, differing substantially from the previously reported value of -0.2 obtained from data with a less sensitive assay. This steep leaving group dependence is consistent with a largely dissociative transition state for AP-catalyzed hydrolysis of

  12. Safety assessment of alkyl benzoates as used in cosmetics.

    PubMed

    'Becker, Lillian C; Bergfeld, Wilma F; Belsito, Donald V; Hill, Ronald A; Klaassen, Curtis D; Liebler, Daniel; Marks, James G; Shank, Ronald C; Slaga, Thomas J; Snyder, Paul W; Andersen, F Alan

    2012-01-01

    The functions of alkyl benzoates in cosmetics include fragrance ingredients, skin-conditioning agents--emollient, skin-conditioning agents--miscellaneous, preservatives, solvents, and plasticizers. The Cosmetic Ingredient Review Expert Panel reviewed the relevant animal and human data and noted gaps in the available safety data for some of the alkyl benzoates. Similar structure activity relationships, biologic functions, and cosmetic product usage allowed the available data of many of the alkyl benzoates to be extended to the entire group. Carcinogenicity data were not available, but available data indicated that these alkyl benzoate cosmetic ingredients are not genotoxic. Also benzoic acid and tested component alcohols were not reproductive or developmental toxicants, are not genotoxic in almost all assays, and are not carcinogenic. These ingredients were determined to be safe in the present practices of use and concentration.

  13. Fluorinated Alkyl Ether Epoxy Resin Compositions and Applications Thereof

    NASA Technical Reports Server (NTRS)

    Wohl, Christopher J. (Inventor); Connell, John W. (Inventor); Smith, Joseph G. (Inventor); Siochi, Emilie J. (Inventor); Gardner, John M. (Inventor); Palmieri, Frank M. (Inventor)

    2017-01-01

    Epoxy resin compositions prepared using amino terminated fluoro alkyl ethers. The epoxy resin compositions exhibit low surface adhesion properties making them useful as coatings, paints, moldings, adhesives, and fiber reinforced composites.

  14. Regeneration of a deactivated USY alkylation catalyst using supercritical isobutane

    SciTech Connect

    Daniel M. Ginosar; David N. Ghompson; Kyle C. Burch

    2005-01-01

    Off-line, in-situ alkylation activity recovery from a completely deactivated solid acid catalyst was examined in a continuous-flow reaction system employing supercritical isobutane. A USY zeolite catalyst was initially deactivated during the liquid phase alkylation of butene with isobutane in a single-pass reactor and then varying amounts of alkylation activity were recovered by passing supercritical isobutane over the catalyst bed at different reactivation conditions. Temperature, pressure and regeneration time were found to play important roles in the supercritical isobutane regeneration process when applied to a completely deactivated USY zeolite alkylation catalyst. Manipulation of the variables that influence solvent strength, diffusivity, surface desorption, hydride transfer rates, and coke aging, strongly influence regeneration effectiveness.

  15. Alkyl chains acting as entropy reservoir in liquid crystalline materials.

    PubMed

    Sorai, Michio; Saito, Kazuya

    2003-01-01

    The roles played by the conformational disordering of alkyl chains in determining the aggregation states of matter are reviewed for liquid crystalline materials from a thermodynamic perspective. Entropy, which is one of the most macroscopic concepts but which has a clear microscopic meaning, provides crucial microscopic information for complex systems for which a microscopic description is hard to establish. Starting from structural implication by absolute (third-law) entropy for crystalline solids, the existence of successive phase transitions caused by the successive conformational melting of alkyl chains in discotic mesogens is explained. An experimental basis is given for the "quasi-binary picture" of thermotropic liquid crystals, i.e., the highly disordered alkyl chains behave like a second component (solvent). A novel entropy transfer between the "components" of a molecule and the resulting "alkyl chains as entropy reservoir" mechanism are explained for cubic mesogens.

  16. Perfluorinated Alkyl Compounds: Challenges To Develop Robust And Reliable Methods

    EPA Science Inventory

    An increasing number of studies have been conducted to investigate the environmental distribution of perfluorinated alkyl compounds (PFCs), some of which are known to be toxic in laboratory studies. Despite growing public concerns, environmental monitoring data are still limited...

  17. Alkylation Induced DNA Repair and Mutagenesis in Escherichia coli.

    DTIC Science & Technology

    1987-11-23

    III (Gates and inn, 1977), Micrococcus luteus UV endo- nuclease (Grossman et al, 1978) and bacteriophage T UV endonuclease (Warner et al, 1980) have DNA...34, Garland Publishing, Inc. New York & London USA. Ather, A., Z. Ahmed and S. Riazxxddin, 1984. Adaptive response of Micrococcus luteus to alkylating...Laval, J., 3. Pierre and F. Laval. 1981. Release of 7-nmthylguanine residues frain alkylated ENA by extracts of Micrococcus luteus and Escherichia

  18. Copper-catalyzed arylation of alkyl halides with arylaluminum reagents

    PubMed Central

    Shrestha, Bijay

    2015-01-01

    Summary We report a Cu-catalyzed coupling between triarylaluminum reagents and alkyl halides to form arylalkanes. The reaction proceeds in the presence of N,N,N’,N’-tetramethyl-o-phenylenediamine (NN-1) as a ligand in combination with CuI as a catalyst. This catalyst system enables the coupling of primary alkyl iodides and bromides with electron-neutral and electron-rich triarylaluminum reagents and affords the cross-coupled products in good to excellent yields. PMID:26734088

  19. Chemoselective Alkylations with N- and C-Metalated Nitriles.

    PubMed

    Yang, Xun; Nath, Dinesh; Fleming, Fraser F

    2015-10-02

    Metalated nitriles exhibit complementary chemoselectivities in electrophilic alkylations. N-Lithiated or C-magnesiated nitriles can be prepared from the same nitrile precursor and selectively reacted with a 1:1 mixture of methyl cyanoformate and benzyl bromide or bifunctional electrophiles through chemoselective attack onto either an alkyl halide or a carbonyl electrophile. A mechanistic explanation for the chemoselectivity preferences is provided that rests on the structural and complexation differences between N- and C-metalated nitriles.

  20. Chemically induced Parkinson's disease: intermediates in the oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine to the 1-methyl-4-phenyl-pyridinium ion

    SciTech Connect

    Chacon, J.N.; Chedekel, M.R.; Land, E.J.; Truscott, T.G.

    1987-04-29

    Various unstable intermediate oxidation states have been postulated in the metabolic activation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine to the 1-methyl-4-phenyl pyridinium ion. We now report the first direct observation of these free radical intermediates by pulse radiolysis and flash photolysis. Studies are described of various reactions of such species, in particular with dopamine whose autoxidation to dopamine quinone is reported to be potentiated by 1-methyl-4-phenyl-1,2,3, 6-tetrahydropyridine.

  1. Final Technical Report [Development of Catalytic Alkylation and Fluoroalkylation Methods

    SciTech Connect

    Vicic, David A.

    2014-05-01

    In the early stages of this DOE-funded research project, we sought to prepare and study a well-defined nickel-alkyl complex containing tridentate nitrogen donor ligands. We found that reaction of (TMEDA)NiMe2 (1) with terpyridine ligand cleanly led to the formation of (terpyridyl)NiMe (2), which we also determined to be an active alkylation catalyst. The thermal stability of 2 was unlike that seen for any of the active pybox ligands, and enabled a number of key studies on alkyl transfer reactions to be performed, providing new insights into the mechanism of nickel-mediated alkyl-alkyl cross-coupling reactions. In addition to the mechanistic studies, we showed that the terpyridyl nickel compounds can catalytically cross-couple alkyl iodides in yields up to 98% and bromides in yields up to 46 %. The yields for the bromides can be increased up to 67 % when the new palladium catalyst [(tpy’)Pd-Ph]I is used. The best route to the targeted [(tpy)NiBr] (1) was found to involve the comproportionation reaction of [(dme)NiBr{sub 2}] and [Ni(COD){sub 2}] in the presence of two equivalents of terpyridine. This reaction was driven to high yields of product formation (72 % isolated) by the precipitation of 1 from THF solvent.

  2. Effects of alkyl substituents of xanthine on phosphodiesterase isoenzymes.

    PubMed

    Miyamoto, K; Sakai, R; Kurita, M; Ohmae, S; Sanae, F; Sawanishi, H; Hasegawa, T; Takagi, K

    1995-03-01

    The structure-activity relationships of a series of alkylxanthine derivatives were investigated. The partition coefficient of alkylxanthines enlarged with an elongation of the alkyl chain at the 1-, 3-, or 7-position of xanthine. There was a mild correlation between the apparent partition coefficient and the tracheal relaxant activity or the inhibitory activity on phosphodiesterase (PDE) IV isoenzyme, while the tracheal relaxant activity closely correlated with the PDE IV inhibitory activity. Regarding substituents at different positions, the alkylation at the 3-position increased the inhibitory activity on every PDE isoenzyme. The alkylation at the 1-position potentiated the inhibitory activity on PDE IV with the alkyl chain length, but decreased the activities on other PDE isoenzymes. The alkylation at the 7-position was characteristic in its decrease in inhibitory activity on PDE III. These results suggested that the potency of the inhibitory activity of xanthine derivatives on PDE isoenzymes is not dependent simply upon their hydrophobicity but upon change in the affinity for the active sites on PDE isoenzymes by the introduction of the alkyl group at particular positions of the xanthine skeleton.

  3. Regioselective 1-N-Alkylation and Rearrangement of Adenosine Derivatives.

    PubMed

    Oslovsky, Vladimir E; Drenichev, Mikhail S; Mikhailov, Sergey N

    2015-01-01

    Several methods for the preparation of some N(6)-substituted adenosines based on selective 1-N-alkylation with subsequent Dimroth rearrangement were developed. The proposed methods seem to be effective for the preparation of natural N(6)-isopentenyl- and N(6)-benzyladenosines, which are known to possess pronounced biological activities. Direct 1-N-alkylation of 2',3',5'-tri-O-acetyladenosine and 3',5'-di-O-acetyl-2'-deoxyadenosine with alkyl halides in N,N-dimethylformamide (DMF) in the presence of BaCO3 and KI gave 1-N-substituted derivatives with quantitative yields, whereas 1-N-alkylation of adenosine was accompanied by significant O-alkylation. Moreover, the reaction of trimethylsilyl derivatives of N(6)-acetyl-2',3',5'-tri-O-acetyladenosine and N(6)-acetyl-3',5'-di-O-acetyl-2'-deoxyadenosine with alkyl halides leads to the formation of the stable 1-N-substituted adenosines. Dimroth rearrangement of 1-N-substituted adenosines in aqueous ammonia yields pure N(6)-substituted adenosines.

  4. Benefits of the stirred, autorefrigerated reactor in sulfuric acid alkylation

    SciTech Connect

    Ackerman, S.; Lerner, H.; Zaczepinski, S.

    1996-12-01

    Alkylation is a process which combines propylenes, butylenes, and pentylenes with isobutane in the presence of an acid catalyst (H{sub 2}SO{sub 4} or HF) to produce a premium quality gasoline blendstock. The alkylation process was developed in the late 1930`s and processing capacity grew tremendously during World War II in response to demand for aviation gasoline. Since that time, alkylation capacity has steadily grown to supply an important motor gasoline component. Now, more than 50 years later, alkylation is in the spotlight again for reformulated gasoline. Alkylate is a high octane, low sensitivity, low RVP, totally paraffinic material which represents the ideal blendstock for modern gasoline manufacture. Two types of modern reactor systems are currently offered for license to the refining industry for sulfuric acid alkylation. These are the stirred, autorefrigerated system offered by Exxon Research and Engineering (ERE) and the indirect, or effluent refrigerated system offered by others. By means of a case study example, this paper discusses the autorefrigerated reaction system and its benefits.

  5. Alcohols as alkylating agents in heteroarene C–H functionalization

    PubMed Central

    Jin, Jian; MacMillan, David W. C.

    2015-01-01

    Redox processes and radical intermediates are found in many biochemical processes, including deoxyribonucleotide synthesis and oxidative DNA damage1. One of the core principles that underlies DNA biosynthesis is the radical-mediated elimnation of H2O to deoxygenate ribonucleotides, an example of ‘spin-center shift’ (SCS)2, during which an alcohol C–O bond is cleaved, resulting in a carbon-centered radical intermediate. While SCS is a well-understood biochemical process, it is underutilized by the synthetic organic chemistry community. We wondered whether it would be possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylations using alcohols as radical precursors. Considering traditional radical-based alkylation methods require the use of stoichiometric oxidants, elevated temperatures, or peroxides3–7, the development of a mild protocol using simple and abundant alkylating agents would have significant utility in the synthesis of diversely functionalized pharmacophores. In this manuscript, we describe the successful execution of this idea via the development of a dual catalytic alkylation of heteroarenes using alcohols as mild alkylating reagents. This method represents the first broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer (HAT) catalysis. The utility of this multi-catalytic protocol has been demonstrated through the late-stage functionalization of the medicinal agents, fasudil and milrinone. PMID:26308895

  6. Alcohols as alkylating agents in heteroarene C-H functionalization

    NASA Astrophysics Data System (ADS)

    Jin, Jian; MacMillan, David W. C.

    2015-09-01

    Redox processes and radical intermediates are found in many biochemical processes, including deoxyribonucleotide synthesis and oxidative DNA damage. One of the core principles underlying DNA biosynthesis is the radical-mediated elimination of H2O to deoxygenate ribonucleotides, an example of `spin-centre shift', during which an alcohol C-O bond is cleaved, resulting in a carbon-centred radical intermediate. Although spin-centre shift is a well-understood biochemical process, it is underused by the synthetic organic chemistry community. We wondered whether it would be possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors. Because conventional radical-based alkylation methods require the use of stoichiometric oxidants, increased temperatures or peroxides, a mild protocol using simple and abundant alkylating agents would have considerable use in the synthesis of diversely functionalized pharmacophores. Here we describe the development of a dual catalytic alkylation of heteroarenes, using alcohols as mild alkylating reagents. This method represents the first, to our knowledge, broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. The value of this multi-catalytic protocol has been demonstrated through the late-stage functionalization of the medicinal agents, fasudil and milrinone.

  7. DNA minor groove targeted alkylating agents based on bisbenzimidazole carriers: synthesis, cytotoxicity and sequence-specificity of DNA alkylation.

    PubMed

    Smaill, J B; Fan, J Y; Denny, W A

    1998-12-01

    A series of bisbenzimidazoles bearing a variety of alkylating agents [ortho- and meta-mustards, imidazolebis(hydroxymethyl), imidazolebis(methylcarbamate) and pyrrolebis(hydroxymethyl)], appended by a propyl linker chain, were prepared and investigated for sequence-specificity of DNA alkylation and their cytotoxicity. Previous work has shown that, for para-aniline mustards, a propyl linker is optimal for cytotoxicity. Alkaline cleavage assays using a variety of different labelled oligonucleotides showed that the preferred sequences for adenine alkylation were 5'-TTTANANAANN and 5'-ATTANANAANN (underlined bases show the drug alkylation sites), with AT-rich sequences required on both the 5' and 3' sides of the alkylated adenine. The different aniline mustards showed little variation in alkylation pattern and similar efficiencies of DNA cross-link formation despite the changes in orientation and positioning of the mustard, suggesting that the propyl linker has some flexibility. The imidazole- and pyrrolebis(hydroxymethyl) alkylators showed no DNA strand cleavage following base treatment, indicating that no guanine or adenine N3 or N7 adducts were formed. Using the PCR-based polymerase stop assay, these alkylators showed PCR blocks at 5'-C*G sites (the * nucleotide indicates the blocked site), particularly at 5'-TAC*GA 5'-AGC*GGA, and 5'-AGCC*GGT sequences, caused by guanine 2-NH2 lesions on the opposite strand. Only the (more reactive) imidazolebis(methylcarbamoyl) and pyrrolebis(hydroxymethyl) alkylators demonstrated interstrand cross-linking ability. All of the bifunctional mustards showed large (approximately 100-fold) increases in cytotoxicity over chlorambucil, with the corresponding monofunctional mustards being 20- to 60-fold less cytotoxic. These results suggest that in the mustards the propyl linker provides sufficient flexibility to achieve delivery of the alkylator to favoured (adenine N3) sites in the minor groove, regardless of its exact geometry with

  8. Polymerization of Conducting Polymers Confined to Free Surfaces: A comparison of the Langmuir-Blodgett Polymerization of 3-Alkyl Pyrroles and 2- Alkyl Anilines

    DTIC Science & Technology

    1992-05-19

    Confined to Free Surfaces: A Comparison of the Langmuir-Blodgett Polymerization of 3- Alkyl Pyrroles and 2- Alkyl Anilines Submitted for Publication in...Surfaces: A Comparison of the Langmuir Blodgett Polymerizations of 3- alkyl pyrroles and 2- alkyl anilines R. S. Duran and H.C. Zhou Dept. of Chemistry...polymerization reactions in more detail and compare them. To do this, the polymerization reactions were run under two conditions. In the first case

  9. Combustion Pathways of the Alkylated Heteroaromatics: Bond Dissociation Enthalpies and Alkyl Group Fragmentations

    NASA Astrophysics Data System (ADS)

    Hayes, Carrigan J.; Hadad, Christopher M.

    2009-04-01

    The bond dissociation enthalpies (BDEs) of the alkyl groups of the alkyl-substituted heterocycles have been studied and compiled using DFT methodology, with the intent of modeling the larger heterocyclic functionalities found in coal. DFT results were calibrated against CBS-QB3 calculations, and qualitative trends were reproduced between these methods. Loss of hydrogen at the benzylic position provided the most favorable route to radical formation, for both the azabenzenes and five-membered heterocycles. The ethyl derivatives had lower BDE values than the methyl derivatives due to increased stabilization of the corresponding radicals. Calculated spin densities correlated well with bond dissociation enthalpies for these compounds, while geometric effects were minimal with respect to the heterocycles themselves. Temperature effects on the bond dissociation enthalpies were minor, ranging by about 5 kcal/mol from 298 to 2000 K; the free energies of reaction dropped significantly over the same range due to entropic effects. Monocyclic heteroaromatic rings were seen to replicate the chemistry of multicyclic heteroaromatic systems.

  10. Early Transition Metal Alkyl and Tetrahydroborate Complexes.

    NASA Astrophysics Data System (ADS)

    Jensen, James Allen

    1988-06-01

    An investigation of early transition metal alkyl and tetrahydroborate complexes as catalytic models and ceramic precursors has been initiated. The compounds MX _2 (dmpe)_2, dmpe = 1,2-bis(dimethylphosphino)ethane, for M = Ti, V, Cr, and X = Br, I, BH_4, have been prepared. These complexes are paramagnetic and have been shown by X-ray crystallography to have trans-octahedral structures. The BH_4^{-} groups in Ti(BH_4)_2(dmpe) _2 bond to the metal in a bidentate manner. This structure is in marked contrast to the structure of the vanadium analogue, V(BH_4)_2 (dmpe)_2, which displays two unidentate BH_4^{-} groups. Alkylation of Ti(BH_4)_2 (dmpe)_2 with LiMe results in the complex TiMe_2(dmpe) _2 which is diamagnetic in both solution and solid state. Single crystal X-ray and neutron diffraction studies show that there may be strong Ti-C pi -bonding. A tetragonal compression along the C -Ti-C bond vector accounts for the observed diamegnetism. A series of complexes of the formula Ti(BH _4)_3(PR_3)_2 has been prepared where PR_3 = PMe_3, PEt_3, PMe_3Ph, and P(OMe)_3 . The X-ray crystal structure of Ti(BH _4)_3(PMe_3)_2 reveals a pseudo trigonal bipyramidal geometry in which two BH_4^{-} groups display an unusual "side-on" bonding mode. The "side-on" ligation mode has been attributed to a Jahn-Teller distortion of the orbitally degenerate d^1 ground state. In contrast, the non-Jahn-Teller susceptible vanadium analogue, V(BH_4)_3 (PMe_3)_2, possesses a nearly ideal D_{rm 3h} >=ometry with three bidentate tetrahydroborate groups. Addition of excess PMe_3 to V(BH_4)_3(PMe _3)_2<=ads to the vanadium(II) hydride -bridged dimer (V(H)(BH_4)(PMe _3)_2]_2, while addition of PMe_3 and water forms the vanadium(III) oxo dimer (V(BH_4)_2 (PMe_3)_2]_2 [mu-O) which has been structurally characterized. The compound Ti(CH_2CMe _3)_4 can be prepared by addition of Ti(OEt)_4 to LiCH_2 CMe_3. Sublimation of Ti(CH _2CMe_3)_4 over a substrate heated to 250^ circC results in the chemical vapor

  11. Synthesis and Modification of Carboxylated Polyphenylenes and Phenylated Polyimides

    DTIC Science & Technology

    1976-03-01

    Aromatic ionomers , Polypyridine, Phenylated polyimides. Acetylene-terminated polyphenylenes, >Thermally-stable polymers. 20. AB8Jj«ACT (Continue on...barium salts to afford a series of aromatic ionomers ^ All but one of the potassium ionomers are soluble in dimethylsulfoxide andrcan be cast into...thin films that tough, flexible, water white, and transparent.Uiie magnesium and barium ionomers are insoluble in common organic solvents)>rhermo

  12. Synthesis of 2-(substituted phenyl)-3,5,5-trimethylmorpholine analogues and their effects on monoamine uptake, nicotinic acetylcholine receptor function, and behavioral effects of nicotine.

    PubMed

    Carroll, F Ivy; Muresan, Ana Z; Blough, Bruce E; Navarro, Hernán A; Mascarella, S Wayne; Eaton, J Brek; Huang, Xiaodong; Damaj, M Imad; Lukas, Ronald J

    2011-03-10

    Toward development of smoking cessation aids superior to bupropion (2), we describe synthesis of 2-(substituted phenyl)-3,5,5-trimethylmorpholine analogues 5a-5h and their effects on inhibition of dopamine, norepinephrine, and serotonin uptake, nicotinic acetylcholine receptor (nAChR) function, acute actions of nicotine, and nicotine-conditioned place preference (CPP). Several analogues encompassing aryl substitutions, N-alkylation, and alkyl extensions of the morpholine ring 3-methyl group provided analogues more potent in vitro than (S,S)-hydroxybupropion (4a) as inhibitors of dopamine or norepinephrine uptake and antagonists of nAChR function. All of the new (S,S)-5 analogues had better potency than (S,S)-4a as blockers of acute nicotine analgesia in the tail-flick test. Two analogues with highest potency at α3β4*-nAChR and among the most potent transporter inhibitors have better potency than (S,S)-4a in blocking nicotine-CPP. Collectively, these findings illuminate mechanisms of action of 2 analogues and identify deshydroxybupropion analogues 5a-5h as possibly superior candidates as aids to smoking cessation.

  13. Palladium-Catalyzed Cross Coupling of Secondary and Tertiary Alkyl Bromides with a Nitrogen Nucleophile

    PubMed Central

    2016-01-01

    We report a new class of catalytic reaction: the thermal substitution of a secondary and or tertiary alkyl halide with a nitrogen nucleophile. The alkylation of a nitrogen nucleophile with an alkyl halide is a classical method for the construction of C–N bonds, but traditional substitution reactions are challenging to achieve with a secondary and or tertiary alkyl electrophile due to competing elimination reactions. A catalytic process could address this limitation, but thermal, catalytic coupling of alkyl halides with a nitrogen nucleophile and any type of catalytic coupling of an unactivated tertiary alkyl halide with a nitrogen nucleophile are unknown. We report the coupling of unactivated secondary and tertiary alkyl bromides with benzophenone imines to produce protected primary amines in the presence of palladium ligated by the hindered trialkylphosphine Cy2t-BuP. Mechanistic studies indicate that this amination of alkyl halides occurs by a reversible reaction to form a free alkyl radical. PMID:27725963

  14. Oxygen Substituent Effects in the Pyrolysis of Phenethyl Phenyl Ethers

    SciTech Connect

    Britt, Phillip F; Kidder, Michelle; Buchanan III, A C

    2007-01-01

    The dominant structural linkage in the abundant renewable energy resource, lignin, is the arylglycerol-{beta}-aryl ether commonly referred to as the {beta}-O-4 linkage. The simplest representation of this linkage, unadorned by substituents, is phenethyl phenyl ether (PhCH{sub 2}CH{sub 2}OPh; PPE). Our prior detailed kinetic studies of the pyrolysis of PPE at 330-425 C showed that a free-radical chain mechanism is involved that cycles through radicals formed at both the {alpha}- and {beta}-carbons. The previously unrecognized competing path involving rearrangement of the {beta}-carbon radical by an O,C-phenyl shift accounts for ca. 25% of the products. In this paper, we explore the effect of aromatic hydroxy and methoxy substituents on both the rate and product selectivity for the pyrolysis of these more complex lignin model compounds. The pyrolysis reactions are conducted in biphenyl solvent at 345 C and low conversions to minimize secondary reactions. The pyrolysis rates were found to vary substantially as a function of the substitution pattern. The rearrangement path involving the {beta}-carbon radical and O,C-phenyl shift was found to remain important in all the molecules investigated, and the selectivity for this path also showed a dependence on the substitution pattern.

  15. Separation optimization for the recovery of phenyl ethyl alcohol.

    PubMed

    Priddy, S A; Hanley, T R; Effler, W T

    1999-01-01

    Phenyl ethyl alcohol is a compound that occurs naturally in flower petals and in many common beverages, such as beer. Desire for the floral, rose-like notes imparted by phenyl ethyl alcohol has created a unique niche for this chemical in flavor and fragrance industries. Phenyl ethyl alcohol can be produced by Saccharomyces cerevisiae via bioconversion. Often this method of production results in extremely low yields, thus placing a great deal of importance on recovery and purification of the valuable metabolite. To determine the best method for recovering the chemical, a primary recovery step and a secondary recovery step were developed. The primary recovery step consisted of comparing dead-end filtration with crossflow ultrafiltration. Crossflow ultrafiltration was ultimately selected to filter the fermentation broth because of its high flow rates and low affinity for the product. The secondary recovery step consisted of a comparison of liquid- liquid extraction and hydrophobic resin recovery. The hydrophobic resin was selected because of its higher rate of recovery and a higher purity than the liquid-liquid extraction, the current practice of Brown-Forman.

  16. 3-Heterocycle-phenyl N-alkylcarbamates as FAAH inhibitors: design, synthesis and 3D-QSAR studies.

    PubMed

    Käsnänen, Heikki; Myllymäki, Mikko J; Minkkilä, Anna; Kataja, Antti O; Saario, Susanna M; Nevalainen, Tapio; Koskinen, Ari M P; Poso, Antti

    2010-02-01

    Carbamates are a well-established class of fatty acid amide hydrolase (FAAH) inhibitors. Here we describe the synthesis of meta-substituted phenolic N-alkyl/aryl carbamates and their in vitro FAAH inhibitory activities. The most potent compound, 3-(oxazol-2yl)phenyl cyclohexylcarbamate (2 a), inhibited FAAH with a sub-nanomolar IC(50) value (IC(50)=0.74 nM). Additionally, we developed and validated three-dimensional quantitative structure-activity relationships (QSAR) models of FAAH inhibition combining the newly disclosed carbamates with our previously published inhibitors to give a total set of 99 compounds. Prior to 3D-QSAR modeling, the degree of correlation between FAAH inhibition and in silico reactivity was also established. Both 3D-QSAR methods used, CoMSIA and GRID/GOLPE, produced statistically significant models with coefficient of correlation for external prediction (R(2) (PRED)) values of 0.732 and 0.760, respectively. These models could be of high value in further FAAH inhibitor design.

  17. Interaction between alkyl radicals and single wall carbon nanotubes.

    PubMed

    Denis, Pablo A

    2012-06-30

    The addition of primary, secondary, and tertiary alkyl radicals to single wall carbon nanotubes (SWCNTs) was studied by means of dispersion corrected density functional theory. The PBE, B97-D, M06-L, and M06-2X functionals were used. Consideration of Van der Waals interactions is essential to obtain accurate addition energies. In effect, the enthalpy changes at 298 K, for the addition of methyl, ethyl, isopropyl, and tert-butyl radicals onto a (5,5) SWCNT are: -25.7, -25.1, -22.4, and -16.6 kcal/mol, at the M06-2X level, respectively, whereas at PBE/6-31G* level they are significantly lower: -25.0, -19.0, -16.7, and -5.0 kcal/mol respectively. Although the binding energies are small, the attached alkyl radicals are expected to be stable because of the large desorption barriers. The importance of nonbonded interactions was more noticeable as we moved from primary to tertiary alkyl radicals. Indeed, for the tert-butyl radical, physisorption onto the (11,0) SWCNT is preferred rather than chemisorption. The bond dissociation energies determined for alkyl radicals and SWCNT follow the trend suggested by the consideration of radical stabilization energies. However, they are in disagreement with some degrees of functionalization observed in recent experiments. This discrepancy would stem from the fact that for some HiPco nanotubes, nonbonded interactions with alkyl radicals are stronger than covalent bonds.

  18. Effects of alkyl substitutions of xanthine skeleton on bronchodilation.

    PubMed

    Sakai, R; Konno, K; Yamamoto, Y; Sanae, F; Takagi, K; Hasegawa, T; Iwasaki, N; Kakiuchi, M; Kato, H; Miyamoto, K

    1992-10-30

    Structure-activity relationships in a series of 1,3,7-trialkyl-xanthine were studied with guinea pigs. Relaxant actions in the tracheal muscle were increased with alkyl chain length at the 1- and 3-positions of the xanthine skeleton, but decreased by alkylation at the 7-position. Positive chronotropic actions in the right atrium were potentiated with 3-alkyl chain length but tended to decrease with 1-alkylation and diminish by 7-substitution. Consequently, while the 1- and 3-substitutions were equally important for the tracheal smooth muscle relaxation, the substitution at the 1-position was more important than the 3-substitution for bronchoselectivity. The 7-alkylation may be significant to cancel heart stimulation. There were good correlations between the smooth muscle relaxant action and the cyclic AMP-PDE inhibitory activity in 3-substituents and the affinity for adenosine (A1) receptors in 1-, 3-, and 7-substituents. This suggests that not only the cyclic AMP-PDE inhibitory activity but also the adenosine antagonistic activity is important in the bronchodilatory effects of alkylxanthines. Among these xanthine derivatives, 1-butyl-3-propylxanthine and its 7-methylated derivative showed high bronchoselectivity in the in vitro and in vivo experiments compared to theophylline and enprofylline and may be new candidates for bronchodilator.

  19. Alkyl polycyclic aromatic hydrocarbons emissions in diesel/biodiesel exhaust

    NASA Astrophysics Data System (ADS)

    Casal, Carina S.; Arbilla, Graciela; Corrêa, Sergio M.

    2014-10-01

    Polycyclic aromatic hydrocarbons (PAHs) are widely studied in environmental matrices, such as air, water, soil and sediment, because of their toxicity, mutagenicity and carcinogenicity. Because of these properties, the environmental agencies of developed countries have listed sixteen PAHs as priority pollutants. Few countries have limits for these compounds for ambient air, but they only limit emissions from stationary and mobile sources and occupational areas. There are several studies to specifically address the 16 priority PAHs and very little for the alkyl PAHs. These compounds are more abundant, more persistent and frequently more toxic than the non-alkylated PAHs, and the toxicity increases with the number of alkyl substitutions on the aromatic ring. In this study, a method was developed for the analysis of PAHs and alkyl PAHs by using a GC-MS and large injection volume injection coupled with program temperature vaporisation, which allows for limits of detection below 1.0 ng μL-1. Several variables were tested, such as the injection volume, injection velocity, injector initial temperature, duration of the solvent split and others. This method was evaluated in samples from particulate matter from the emissions of engines employing standard diesel, commercial diesel and biodiesel B20. Samples were collected on a dynamometer bench for a diesel engine cycle and the results ranged from 0.5 to 96.9 ng mL-1, indicating that diesel/biodiesel makes a significant contribution to the formation of PAHs and alkyl PAHs.

  20. General allylic C-H alkylation with tertiary nucleophiles.

    PubMed

    Howell, Jennifer M; Liu, Wei; Young, Andrew J; White, M Christina

    2014-04-16

    A general method for intermolecular allylic C-H alkylation of terminal olefins with tertiary nucleophiles has been accomplished employing palladium(II)/bis(sulfoxide) catalysis. Allylic C-H alkylation furnishes products in good yields (avg. 64%) with excellent regio- and stereoselectivity (>20:1 linear:branched, >20:1 E:Z). For the first time, the olefin scope encompasses unactivated aliphatic olefins as well as activated aromatic/heteroaromatic olefins and 1,4-dienes. The ease of appending allyl moieties onto complex scaffolds is leveraged to enable this mild and selective allylic C-H alkylation to rapidly diversify phenolic natural products. The tertiary nucleophile scope is broad and includes latent functionality for further elaboration (e.g., aliphatic alcohols, α,β-unsaturated esters). The opportunities to effect synthetic streamlining with such general C-H reactivity are illustrated in an allylic C-H alkylation/Diels-Alder reaction cascade: a reactive diene is generated via intermolecular allylic C-H alkylation and approximated to a dienophile contained within the tertiary nucleophile to furnish a common tricyclic core found in the class I galbulimima alkaloids.

  1. Synthesis and evaluation of novel 3-C-alkylated-Neu5Ac2en derivatives as probes of influenza virus sialidase 150-loop flexibility.

    PubMed

    Rudrawar, Santosh; Kerry, Philip S; Rameix-Welti, Marie-Anne; Maggioni, Andrea; Dyason, Jeffrey C; Rose, Faith J; van der Werf, Sylvie; Thomson, Robin J; Naffakh, Nadia; Russell, Rupert J M; von Itzstein, Mark

    2012-11-21

    Novel 3-C-alkylated-Neu5Ac2en derivatives have been designed to target the expanded active site cavity of influenza virus sialidases with an open 150-loop, currently seen in X-ray crystal structures of influenza A virus group-1 (N1, N4, N5, N8), but not group-2 (N2, N9), sialidases. The compounds show selectivity for inhibition of H5N1 and pdm09 H1N1 sialidases over an N2 sialidase, providing evidence of the relative 150-loop flexibility of these sialidases. In a complex with N8 sialidase, the C3 substituent of 3-phenylally-Neu5Ac2en occupies the 150-cavity while the central ring and the remaining substituents bind the active site as seen for the unsubstituted template. This new class of inhibitors, which can 'trap' the open 150-loop form of the sialidase, should prove useful as probes of 150-loop flexibility.

  2. Selective N-Alkylation of Aniline by Micellar Catalysis

    PubMed

    Siswanto; Rathman

    1997-12-01

    Reactions of aniline with 1-bromobutane to form N-butylaniline and N,N-dibutylaniline were performed in single-phase aqueous surfactant systems. Reaction rate, yield, and selectivity of the N-alkyl product were monitored for different initial compositions, and much higher reaction rate, yield, and selectivity were observed in comparison to reactions of neat components. Excess aniline increased yield and selectivity, while excess 1-bromobutane had the opposite effect. The lipophilic reactant (1-bromobutane) and both products are solubilized almost entirely in the surfactant micelles. The formation of relatively small amounts of N,N-dibutylaniline effectively inhibited further alkylation of N-butylaniline, so that high selectivities (>20) of the N-alkyl were obtained. Added sodium hydroxide caused small decreases in yield and selectivity and showed that pH-dependent dissociation equilibria of the various amine species do not have a major influence on reaction characteristics. Copyright 1997 Academic Press. Copyright 1997Academic Press

  3. Electrophilic metal alkyl chemistry in new ligand environments

    SciTech Connect

    Jordan, Richard F.

    2002-09-11

    Cationic group 4 and actinide Cp{sub 2}MR{sup +} metallocenes, and isolobal neutral group 3 and lanthanide Cp{sub 2}MR analogs, are exceptionally reactive in insertion and {sigma}-bond metathesis processes, and have been exploited extensively in catalysis and synthesis, most notably single-site olefin polymerization. The objectives of recent work were to design new electrophilic metal alkyls based on non-Cp{sub 2}M structures, and to exploit these systems in fundamental and applied studies related to olefin polymerization and other catalytic reactions. Key results are reported in the following areas: discrete non-metallocene cationic group 4 alkyls, activation of non-metallocene compounds with methylalumoxane, and cationic aluminum alkyl compounds. Numerous structural formulas are included.

  4. Saturation anomalies of alkyl nitrates in the tropical Pacific Ocean

    NASA Astrophysics Data System (ADS)

    Dahl, Elizabeth E.; Yvon-Lewis, Shari A.; Saltzman, Eric S.

    2005-10-01

    This paper reports the first measurements of the saturation state of low molecular weight alkyl nitrates (methyl, ethyl, isopropyl, and n-propyl nitrate) in the tropical Pacific Ocean. These compounds were supersaturated with saturation anomalies as high as 2000%. Air/sea flux estimates based on these measurements suggest that surface ocean emissions are sufficient to account for observed levels of tropospheric alkyl nitrates in this region. Model calculations suggest that atmospheric loss rates are faster than can be explained by photolysis and reaction with OH alone. The implication is that removal via transport is important, and there must be a net export of alkyl nitrates from the tropics to other regions of the atmosphere.

  5. Safety Assessment of Alkyl PEG Sulfosuccinates as Used in Cosmetics.

    PubMed

    Johnson, Wilbur; Heldreth, Bart; Bergfeld, Wilma F; Belsito, Donald V; Hill, Ronald A; Klaassen, Curtis D; Liebler, Daniel C; Marks, James G; Shank, Ronald C; Slaga, Thomas J; Snyder, Paul W; Andersen, F Alan

    2015-09-01

    The Cosmetic Ingredient Review (CIR) Expert Panel (Panel) reviewed the safety of alkyl polyethylene glycol (PEG) sulfosuccinates, which function in cosmetics mostly as surfactants/cleansing agents. Although these ingredients may cause ocular and skin irritation, dermal penetration is unlikely because of the substantial polarity and molecular size of these ingredients. The Panel considered the negative oral carcinogenicity and reproductive and developmental toxicity data on chemically related laureths (PEG lauryl ethers) and negative repeated dose toxicity and skin sensitization data on disodium laureth sulfosuccinate supported the safety of these alkyl PEG sulfosuccinates in cosmetic products, but. The CIR Expert Panel concluded that the alkyl PEG sulfosuccinates are safe in the present practices of use and concentration when formulated to be nonirritating.

  6. Safety Assessment of Alkyl Ethylhexanoates as Used in Cosmetics.

    PubMed

    Fiume, Monice; Heldreth, Bart; Bergfeld, Wilma F; Belsito, Donald V; Hill, Ronald A; Klaassen, Curtis D; Liebler, Daniel C; Marks, James G; Shank, Ronald C; Slaga, Thomas J; Snyder, Paul W; Andersen, F Alan

    2015-01-01

    The Cosmetic Ingredient Review (CIR) Expert Panel (Panel) assessed the safety of 16 alkyl ethylhexanoates for use in cosmetics, concluding that these ingredients are safe in cosmetic formulations in the present practices of use and concentrations when formulated to be nonirritating. The alkyl ethylhexanoates primarily function as skin-conditioning agents in cosmetics. The highest concentration of use reported for any of the alkyl ethylhexanoates is 77.3% cetyl ethylhexanoate in rinse-off formulations used near the eye, and the highest leave-on use reported is 52% cetyl ethylhexanoate in lipstick formulations. The Panel reviewed available animal and clinical data related to these ingredients, and the similarities in structure, properties, functions, and uses of ingredients from previous CIR assessments on constituent alcohols that allowed for extrapolation of the available toxicological data to assess the safety of the entire group.

  7. Synthesis and reactivity of rare earth metal alkyl complexes stabilized by anilido phosphinimine and amino phosphine ligands.

    PubMed

    Liu, Bo; Cui, Dongmei; Ma, Jia; Chen, Xuesi; Jing, Xiabin

    2007-01-01

    Anilido phosphinimino ancillary ligand H(2)L(1) reacted with one equivalent of rare earth metal trialkyl [Ln{CH(2)Si(CH(3))(3)}(3)(thf)(2)] (Ln=Y, Lu) to afford rare earth metal monoalkyl complexes [L(1)LnCH(2)Si(CH(3))(3)(THF)] (1 a: Ln=Y; 1 b: Ln=Lu). In this process, deprotonation of H(2)L(1) by one metal alkyl species was followed by intramolecular C--H activation of the phenyl group of the phosphine moiety to generate dianionic species L(1) with release of two equivalnts of tetramethylsilane. Ligand L(1) coordinates to Ln(3+) ions in a rare C,N,N tridentate mode. Complex l a reacted readily with two equivalents of 2,6-diisopropylaniline to give the corresponding bis-amido complex [(HL(1))LnY(NHC(6)H(3)iPr(2)-2,6)(2)] (2) selectively, that is, the C--H activation of the phenyl group is reversible. When 1 a was exposed to moisture, the hydrolyzed dimeric complex [{(HL(1))Y(OH)}(2)](OH)(2) (3) was isolated. Treatment of [Ln{CH(2)Si(CH(3))(3)}(3)(thf)(2)] with amino phosphine ligands HL(2-R) gave stable rare earth metal bis-alkyl complexes [(L(2-R))Ln{CH(2)Si(CH(3))(3)}(2)(thf)] (4 a: Ln=Y, R=Me; 4 b: Ln=Lu, R=Me; 4 c: Ln=Y, R=iPr; 4 d: Ln=Y, R=iPr) in high yields. No proton abstraction from the ligand was observed. Amination of 4 a and 4 c with 2,6-diisopropylaniline afforded the bis-amido counterparts [(L(2-R))Y(NHC(6)H(3)iPr(2)-2,6)(2)(thf)] (5 a: R=Me; 5 b: R=iPr). Complexes 1 a,b and 4 a-d initiated the ring-opening polymerization of d,l-lactide with high activity to give atactic polylactides.

  8. Catalytic reaction of 3-phenyl-2-propyn-1-ol with alcohols

    SciTech Connect

    Grigoryan, S.G.; Avetisyan, K.G.; Matnishyan, A.A.

    1987-01-10

    The cyclic ketal 2,5-dimethyl-2,5-bis(3-phenyl-2-propynyloxy)-1,4-dioxane was obtained by the reaction of 3-phenyl-2-propyn-1=ol with propargyl alcohol in the presence of the HgO-BF/sub 3/ O(C/sub 2/H/sub 5/)/sub 2/ catalytic system. The transformation of 3-phenyl-2-propyn-1-ol and its ethers in methanol and ethanol by the action of the above-mentioned catalytic system leads to 1-phenyl-3-alkoxy-1-propanone, 1-phenyl-1,1,3-trialkoxypropane, and 1-phenyl-2-propen-1-one. The intermediate organomercury compound, which is the product from regioselective addition of mercuric oxide and the saturated alcohol at the triple bond, was isolated. Its protodemercuration led to the above-mentioned linear products. The formation of the cyclic ketal is presumably due to the preferred formation of mercury bis-hydroxypropargylide.

  9. Coal anion structure and chemistry of coal alkylation. Final report, March 1, 1979-February 29, 1980

    SciTech Connect

    Stock, L.M.

    1980-01-01

    In accord with Task 1, some ether cleavage reactions were carried out in two different media - potassium/naphthalene/tetrahydrofuran and potassium/ ammonia - so that the merits and demerits of the two methods could be compared. Preliminary results suggest that both systems yield the same products, and that the ammonia medium is more convenient to work with, because of the absence of by-products such as reduced naphthalenes and tetralin. Dialkyl ethers were found to be least reactive compounds while the benzyl and phenyl ethers were found to be most reactive, as would be expected. The reductive alkylation of coal was carried out in ammonia at 25/sup 0/C. The tetrahydrofuran solubility of the reaction product was surprisingly low. We have obtained additional /sup 13/C)/sup 1/H) nmr data for tetrahydrofuran-soluble butylated coal and some model compounds; obtained additional Styragel(R) chromatography data of tetrahydrofuran-soluble coal labelled with 98%-enriched butyl-1,1-d/sub 2/ iodide; and obtained /sup 2/D nmr spectra of all the deuterium-labelled, tetrahydrofuran-soluble coal products. In accord with Task 4, we have undertaken a review of the information now available concerning the nature of Illinois No. 6 coal. Also, the effects of organic additives on the exchange reactions between tetralin-d/sub 12/ and diphenyl-methane and on the thermal cleavage reactions of several model compounds in tetralin were investigated to probe the relationship between structure and reactivity. The exchange reaction can be accelerated by coal, asphaltene-preasphaltene fractions derived from coal, compounds with labile bonds, or compounds which can be reduced readily. The pyridine-insoluble coal product, acids, and bases are inactive toward the exchange reaction.

  10. Alkyl phospholipid antihypertensive agents in method of lowering blood pressure

    DOEpatents

    Snyder, Fred L.; Blank, Merle L.; Muirhead, Ernest E.; Leach, deceased, Byron E.; Byers, Lawrence W.

    1988-01-01

    The composition of this invention is 1-O-alkyl-2-acetoyl-sn-glycero-3-phosphocholine, having the ionic structural formula; ##STR1## wherein R is saturated alkyl having 9-21 carbon atoms, or salts or hydrates of the composition. Preferably R has 13-19 carbon atoms and most preferably R has 15 carbon atoms. The composition of this invention is useful for reducing hypertension in warm-blooded animals, including humans, when administered either orally or by injection or innoculation, e.g., intravenous injection. The composition can be prepared from naturally occurring lipids or synthetically from commercially available material.

  11. Solid-Phase S-Alkylation Promoted by Molecular Sieves.

    PubMed

    Calce, Enrica; Leone, Marilisa; Mercurio, Flavia Anna; Monfregola, Luca; De Luca, Stefania

    2015-11-20

    A solid-phase S-alkylation procedure to introduce chemical modification on the cysteine sulfhydryl group of a peptidyl resin is reported. The reaction is promoted by activated molecular sieves and consists of a solid-solid process, since both the catalyst and the substrate are in a solid state. The procedure was revealed to be efficient and versatile, particularly when used in combination with the solution S-alkylation approach, allowing for the introduction of different molecular diversities on the same peptide molecule.

  12. Alkyl Azides, Diazides, Haloazides and Bridged Polycyclic Diazides

    DTIC Science & Technology

    1991-05-16

    temperature. Most of the methyl ether was removed during this process. The ehtyl ether was distilled from the reaction mixture using a water aspirator into a...Street PROGRAM IPROJECT ITASK IWORK li1111? ArliiqIoh, VA 22217-5000 EILIMENT NO I NO. I oACCESSION P10) Alkyl Azides, Dlazides, laloazides and...REPRODUCE LEGIBLY. ALKYL AZIDES, DIAZIDES, HALOAZIDES AND BRIDGED POLYCYCLIC DIAZIDES Final REPORTe July 1, 1989-November 14, 1990 A6jd.%4gi0 F’or

  13. Direct β-Alkylation of Aldehydes via Photoredox Organocatalysis

    PubMed Central

    2015-01-01

    Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C–H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable. PMID:24754456

  14. The alkylation of 2′-deoxyguanosine and of thymidine with diazoalkanes. Some observations on O-alkylation

    PubMed Central

    Farmer, P. B.; Foster, A. B.; Jarman, M.; Tisdale, M. J.

    1973-01-01

    The reaction in ether–methanol between 2′-deoxyguanosine and diazomethane or its ethyl or n-butyl homologue gives 1-, O6- and 7-alkyl-2′-deoxyguanosine. N2,O6-Dimethyl-2′-deoxyguanosine was also detected. The hydrolysis of the methyl and the ethyl derivatives gives the corresponding alkylguanines: the O6-alkyl-2′-deoxyguanosines were sequentially hydrolysed, first to 2-amino-6-alkoxypurines, subsequently to guanine. The mass spectra of O6-alkyl-2′-deoxyguanosines (methyl and ethyl) and of the corresponding 2-amino-6-alkoxypurines were determined. The reaction of diazomethane with thymidine afforded O4-methylthymidine, in addition to the previously detected 3-methylthymidine. PMID:4776868

  15. 40 CFR 721.10058 - Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Reaction product of alkylphenol... Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and formaldehyde... identified generically as reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl...

  16. 40 CFR 721.10058 - Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Reaction product of alkylphenol... Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and formaldehyde... identified generically as reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl...

  17. 40 CFR 721.10058 - Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Reaction product of alkylphenol... Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and formaldehyde... identified generically as reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl...

  18. 40 CFR 721.10058 - Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Reaction product of alkylphenol... Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and formaldehyde... identified generically as reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl...

  19. 40 CFR 721.10058 - Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Reaction product of alkylphenol... Reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl dibenzene, and formaldehyde... identified generically as reaction product of alkylphenol, aromatic cyclicamine, alkyl diglycidyl...

  20. Chiral Brønsted Base-Promoted Nitroalkane Alkylation: Enantioselective Synthesis of sec-Alkyl-3-Substituted Indoles

    PubMed Central

    Dobish, Mark C.; Johnston, Jeffrey N.

    2010-01-01

    A Brønsted base-catalyzed reaction of nitroalkanes with alkyl electrophiles provides indole heterocycles substituted at C3 bearing a sec-alkyl group with good enantioselectivity (up to 90% ee). Denitration by hydrogenolysis provides a product with equally high ee. An indolenine intermediate is implicated in the addition step, and surprisingly, water cosolvent was found to have a beneficial effect in this step, leading to a one-pot protocol for elimination/enantioselective addition using PBAM, a bis(amidine) chiral nonracemic base. PMID:21090654

  1. Transition-Metal-Free Regioselective Alkylation of Pyridine N-Oxides Using 1,1-Diborylalkanes as Alkylating Reagents.

    PubMed

    Jo, Woohyun; Kim, Junghoon; Choi, Seoyoung; Cho, Seung Hwan

    2016-08-08

    Reported herein is an unprecedented base-promoted deborylative alkylation of pyridine N-oxides using 1,1-diborylalkanes as alkyl sources. The reaction proceeds efficiently for a wide range of pyridine N-oxides and 1,1-diborylalkanes with excellent regioselectivity. The utility of the developed method is demonstrated by the sequential C-H arylation and methylation of pyridine N-oxides. The reaction also can be applied for the direct introduction of a methyl group to 9-O-methylquinine N-oxide, thus it can serve as a powerful method for late-stage functionalization.

  2. A new strategy for site-specific alkylation of DNA using oligonucleotides containing an abasic site and alkylating probes.

    PubMed

    Sato, Norihiro; Tsuji, Genichiro; Sasaki, Yoshihiro; Usami, Akira; Moki, Takuma; Onizuka, Kazumitsu; Yamada, Ken; Nagatsugi, Fumi

    2015-10-14

    Selective chemical reactions with DNA, such as its labelling, are very useful in many applications. In this paper, we discuss a new strategy for the selective alkylation of DNA using an oligonucleotide containing an abasic site and alkylating probes. We designed three probes consisting of 2-AVP as a reactive moiety and three kinds of binding moiety with high affinity to duplex DNA. Among these probes, Hoechst-AVP probe exhibited high selectivity and efficient reactivity to thymine bases at the site opposite an abasic site in DNA. Our method is potentially useful for inducing site-directed reactions aimed at inhibiting polymerase reactions.

  3. Iron-Catalyzed C-H Alkylation of Heterocyclic C-H Bonds.

    PubMed

    Babu, Kaki Raveendra; Zhu, Nengbo; Bao, Hongli

    2017-01-06

    An efficient, iron-catalyzed C-H alkylation of benzothiazoles by using alkyl diacyl peroxides and alkyl tert-butyl peresters which are readily accessible from carboxylic acids to synthesize 2-alkylbenzothiazoles is developed. This reaction is environmentally benign and compatible with a broad range of functional groups. Various primary, secondary, and tertiary alkyl groups can be efficiently incorporated into diverse benzothiazoles. The effectiveness of this method is illustrated by late-stage functionalization of biologically active heterocycles.

  4. Phase transformation of calcium phenyl phosphate in calcium hydroxyapatite

    SciTech Connect

    Tanaka, Hidekazu . E-mail: hidekazu@riko.shimane-u.ac.jp; Ibaraki, Koshiro; Uemura, Masao; Hino, Ryozi; Kandori, Kazuhiko; Ishikawa, Tatsuo

    2007-07-03

    Calcium phenyl phosphate (CaPP) was synthesized from a mixture of Ca(OH){sub 2} and phenyl phosphate (C{sub 6}H{sub 5}PO{sub 4}H{sub 2}) in an aqueous media. XRD pattern of CaPP exhibited five diffraction peaks at 2{theta} = 6.6, 13.3, 20.0, 26.8 and 33.7{sup o}. The d-spacing ratio of these peaks was ca. 1:1/2:1/3:1/4:1/5. The molar ratios of Ca/P and phenyl/P of CaPP were 1.0 and 0.92, respectively, and the chemical formula of the material was expressed as (C{sub 6}H{sub 5}PO{sub 4}){sub 0.92}(HPO{sub 4}){sub 0.08}Ca.1.3H{sub 2}O, similar to that of dicalcium phosphate dihydrate (CaHPO{sub 4}.2H{sub 2}O: DCPD). These results allowed us to infer that CaPP is composed of a multilayer alternating bilayer of phenyl groups of the phosphates and DCPD-like phase. The structure of the material was essentially not altered after aging at pH 9.0-11.0 and 85 deg. C in an aqueous media. While, after aging at pH {<=}8.0, the diffraction peaks of CaPP were suddenly weakened and disappeared at pH 7.0. Besides, new peaks due to calcium hydroxyapatite (Ca{sub 10}(PO{sub 4}){sub 6}(OH){sub 2}: Hap) appeared and their intensity was strengthened with decreasing the solution pH. TEM observation revealed that the Hap particles formed at pH 6.0 are fibrous with ca. 1.5 {mu}m in length and ca. 0.2 {mu}m in width. From these results, it is presumed that the layered CaPP was dissolved, hydrolyzed and reprecipitated to fibrous Hap particles at pH {<=}8.0 and 85 deg. C in aqueous media. This phase transformation of CaPP in Hap resembled to the formation mechanism of Hap in animal organism.

  5. Acute Oral Toxicity Potential of 4-Nitrophenyl Methkyl Phenyl Phosphinate.

    DTIC Science & Technology

    1982-09-01

    methyl phenyl phosphinate Chemical Abstract Service Registry No.: None Molecular structure: C Ii NO P 13 12 4 .0 0~ NO., CH3 o o...C 56.33 56.17 H 4.36 4.28 N 5.05 5.14 P 11.17 11.25 2. Chemical Name: Polysorbate 80 (Tween 80) Chemical Abstract Service Registry No.: 9005-65-6...administration particularly in chronic toxicity studies in experimental data. 3. Chemical Name: Citric Acid, monohydrate Chemical Abstract Service

  6. A structure-function relationship for the optical modulation of phenyl boronic acid-grafted, polyethylene glycol-wrapped single-walled carbon nanotubes.

    PubMed

    Mu, Bin; McNicholas, Thomas P; Zhang, Jingqing; Hilmer, Andrew J; Jin, Zhong; Reuel, Nigel F; Kim, Jong-Ho; Yum, Kyungsuk; Strano, Michael S

    2012-10-24

    Phenyl boronic acids (PBA) are important binding ligands to pendant diols useful for saccharide recognition. The aromatic ring can also function to anchor an otherwise hydrophilic polymer backbone to the surface of hydrophobic graphene or carbon nanotube. In this work, we demonstrate both functions using a homologous series of seven phenyl boronic acids conjugated to a polyethylene glycol, eight-membered, branched polymer (PPEG8) that allows aqueous dispersion of single-walled carbon nanotubes (SWNT) and quenching of the near-infrared fluorescence in response to saccharide binding. We compare the 2-carboxyphenylboronic acid (2CPBA); 3-carboxy- (3CPBA) and 4-carboxy- (4CPBA) phenylboronic acids; N-(4-phenylboronic)succinamic acid (4SCPBA); 5-bromo-3-carboxy- (5B3CPBA), 3-carboxy-5-fluoro- (5F3CPBA), and 3-carboxy-5-nitro- (5N3CPBA) phenylboronic acids, demonstrating a clear link between SWNT photoluminescence quantum yield and boronic acid structure. Surprisingly, quantum yield decreases systematically with both the location of the BA functionality and the inclusion of electron-withdrawing or -donating substituents on the phenyl ring. For three structural isomers (2CPBA, 3CPBA, and 4CPBA), the highest quantum yields were measured for para-substituted PBA (4CPBA), much higher than ortho- (2CPBA) and meta- (3CPBA) substituted PBA, indicating the first such dependence on molecular structure. Electron-withdrawing substituents such as nitro groups on the phenyl ring cause higher quantum yield, while electron-donating groups such as amides and alkyl groups cause a decrease. The solvatochromic shift of up to 10.3 meV was used for each case to estimate polymer surface coverage on an areal basis using a linear dielectric model. Saccharide recognition using the nIR photoluminescence of SWNT is demonstrated, including selectivity toward pentoses such as arabinose, ribose, and xylose to the exclusion of the expected fructose, which has a high selectivity on PBA due to the

  7. Bis(thienothiophenyl) diketopyrrolopyrrole-based conjugated polymers with various branched alkyl side chains and their applications in thin-film transistors and polymer solar cells.

    PubMed

    Shin, Jicheol; Park, Gi Eun; Lee, Dae Hee; Um, Hyun Ah; Lee, Tae Wan; Cho, Min Ju; Choi, Dong Hoon

    2015-02-11

    New thienothiophene-flanked diketopyrrolopyrrole and thiophene-containing π-extended conjugated polymers with various branched alkyl side-chains were successfully synthesized. 2-Octyldodecyl, 2-decyltetradecyl, 2-tetradecylhexadecyl, 2-hexadecyloctadecyl, and 2-octadecyldocosyl groups were selected as the side-chain moieties and were anchored to the N-positions of the thienothiophene-flanked diketopyrrolopyrrole unit. All five polymers were found to be soluble owing to the bulkiness of the side chains. The thin-film transistor based on the 2-tetradecylhexadecyl-substituted polymer showed the highest hole mobility of 1.92 cm2 V(-1) s(-1) due to it having the smallest π-π stacking distance between the polymer chains, which was determined by grazing incidence X-ray diffraction. Bulk heterojunction polymer solar cells incorporating [6,6]-phenyl-C71-butyric acid methyl ester as the n-type molecule and the additive 1,8-diiodooctane (1 vol %) were also constructed from the synthesized polymers without thermal annealing; the device containing the 2-octyldodecyl-substituted polymer exhibited the highest power conversion efficiency of 5.8%. Although all the polymers showed similar physical properties, their device performance was clearly influenced by the sizes of the branched alkyl side-chain groups.

  8. Synthesis of novel 1,2,3-triazole substituted-N-alkyl/aryl nitrone derivatives, their anti-inflammatory and anticancer activity.

    PubMed

    Sambasiva Rao, P; Kurumurthy, C; Veeraswamy, B; Santhosh Kumar, G; Poornachandra, Y; Ganesh Kumar, C; Vasamsetti, Sathish Babu; Kotamraju, Srigiridhar; Narsaiah, B

    2014-06-10

    A series of novel 1,2,3-triazole substituted N-phenyl nitrone derivatives 5a-e were prepared in three steps starting from 1-substituted-1,2,3-triazole-4-carbaldehydes 2 via Schiff's base formation, reduction followed by oxidation. Similarly, 1,2,3-triazole substituted N-alkyl nitrone derivatives 6a-p were prepared in single step starting from compound 2 on reaction with N-alkyl hydroxylamine hydrochlorides. All the final compounds were screened for anti-inflammatory and anticancer activity against various cancer cell lines. Among the compounds tested, the compounds 5a, 5d, 6a, 6b, 6m and 6o exhibited significant inhibition of IL-1β secretion as a measure of anti-inflammatory activity. Compound 5b, 5c, 6h, 6i and 6o exhibited significant activity against all the cell lines (A549, COLO 205, MDA-MB 231 and PC-3) at IC50 values of <15 μM.

  9. 40 CFR 721.2094 - N,N′-di(alkyl heteromonocycle)amino chlorotriazine.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false N,Nâ²-di(alkyl heteromonocycle)amino... Specific Chemical Substances § 721.2094 N,N′-di(alkyl heteromonocycle)amino chlorotriazine. (a) Chemical... as N,N′-di(alkyl heteromonocycle)amino chlorotriazine (PMN P-93-1369) is subject to reporting...

  10. 40 CFR 721.2094 - N,N′-di(alkyl heteromonocycle)amino chlorotriazine.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false N,Nâ²-di(alkyl heteromonocycle)amino... Specific Chemical Substances § 721.2094 N,N′-di(alkyl heteromonocycle)amino chlorotriazine. (a) Chemical... as N,N′-di(alkyl heteromonocycle)amino chlorotriazine (PMN P-93-1369) is subject to reporting...

  11. 40 CFR 721.2094 - N,N′-di(alkyl heteromonocycle)amino chlorotriazine.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false N,Nâ²-di(alkyl heteromonocycle)amino... Specific Chemical Substances § 721.2094 N,N′-di(alkyl heteromonocycle)amino chlorotriazine. (a) Chemical... as N,N′-di(alkyl heteromonocycle)amino chlorotriazine (PMN P-93-1369) is subject to reporting...

  12. 40 CFR 721.2094 - N,N′-di(alkyl heteromonocycle)amino chlorotriazine.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false N,Nâ²-di(alkyl heteromonocycle)amino... Specific Chemical Substances § 721.2094 N,N′-di(alkyl heteromonocycle)amino chlorotriazine. (a) Chemical... as N,N′-di(alkyl heteromonocycle)amino chlorotriazine (PMN P-93-1369) is subject to reporting...

  13. 40 CFR 721.10548 - Mixed alkyl phosphate esters alkoxylated (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Mixed alkyl phosphate esters... Specific Chemical Substances § 721.10548 Mixed alkyl phosphate esters alkoxylated (generic). (a) Chemical... as mixed alkyl phosphate esters alkoxylated (PMN P-04-624) is subject to reporting under this...

  14. 40 CFR 721.10498 - Substituted alkyl ester, hydrolysis products with silica (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted alkyl ester, hydrolysis... Significant New Uses for Specific Chemical Substances § 721.10498 Substituted alkyl ester, hydrolysis products... chemical substances identified generically as substituted alkyl ester, hydrolysis products with...

  15. 40 CFR 721.6475 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl polycarboxylic acids, esters... Significant New Uses for Specific Chemical Substances § 721.6475 Alkyl polycarboxylic acids, esters with... chemical substances identified generically as alkyl polycarboxylic acids, esters with ethoxylated...

  16. 40 CFR 721.10498 - Substituted alkyl ester, hydrolysis products with silica (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted alkyl ester, hydrolysis... Significant New Uses for Specific Chemical Substances § 721.10498 Substituted alkyl ester, hydrolysis products... chemical substances identified generically as substituted alkyl ester, hydrolysis products with...

  17. 40 CFR 721.6475 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl polycarboxylic acids, esters... Significant New Uses for Specific Chemical Substances § 721.6475 Alkyl polycarboxylic acids, esters with... chemical substances identified generically as alkyl polycarboxylic acids, esters with ethoxylated...

  18. 40 CFR 721.10548 - Mixed alkyl phosphate esters alkoxylated (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Mixed alkyl phosphate esters... Specific Chemical Substances § 721.10548 Mixed alkyl phosphate esters alkoxylated (generic). (a) Chemical... as mixed alkyl phosphate esters alkoxylated (PMN P-04-624) is subject to reporting under this...

  19. 40 CFR 721.6475 - Alkyl polycarboxylic acids, esters with ethoxylated fatty alcohols.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl polycarboxylic acids, esters... Significant New Uses for Specific Chemical Substances § 721.6475 Alkyl polycarboxylic acids, esters with... chemical substances identified generically as alkyl polycarboxylic acids, esters with ethoxylated...

  20. 40 CFR 721.10359 - Cardanol-based alkyl phosphate (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Cardanol-based alkyl phosphate... Specific Chemical Substances § 721.10359 Cardanol-based alkyl phosphate (generic). (a) Chemical substance... cardanol-based alkyl phosphate (PMN P-09-613) is subject to reporting under this section for...

  1. 40 CFR 721.10359 - Cardanol-based alkyl phosphate (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Cardanol-based alkyl phosphate... Specific Chemical Substances § 721.10359 Cardanol-based alkyl phosphate (generic). (a) Chemical substance... cardanol-based alkyl phosphate (PMN P-09-613) is subject to reporting under this section for...

  2. 40 CFR 721.10359 - Cardanol-based alkyl phosphate (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Cardanol-based alkyl phosphate... Specific Chemical Substances § 721.10359 Cardanol-based alkyl phosphate (generic). (a) Chemical substance... cardanol-based alkyl phosphate (PMN P-09-613) is subject to reporting under this section for...

  3. 40 CFR 721.10479 - Quaternary ammonium compounds, tris(hydrogenated tallow alkyl)methyl, chlorides.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...(hydrogenated tallow alkyl)methyl, chlorides. 721.10479 Section 721.10479 Protection of Environment..., tris(hydrogenated tallow alkyl)methyl, chlorides. (a) Chemical substance and significant new uses...(hydrogenated tallow alkyl)methyl, chlorides (PMN P-04-335; CAS No. 308074-73-9) is subject to reporting...

  4. 40 CFR 721.10479 - Quaternary ammonium compounds, tris(hydrogenated tallow alkyl)methyl, chlorides.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...(hydrogenated tallow alkyl)methyl, chlorides. 721.10479 Section 721.10479 Protection of Environment..., tris(hydrogenated tallow alkyl)methyl, chlorides. (a) Chemical substance and significant new uses...(hydrogenated tallow alkyl)methyl, chlorides (PMN P-04-335; CAS No. 308074-73-9) is subject to reporting...

  5. 40 CFR 721.3900 - Alkyl polyethylene glycol phosphate, potassium salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl polyethylene glycol phosphate... Specific Chemical Substances § 721.3900 Alkyl polyethylene glycol phosphate, potassium salt. (a) Chemical... as alkyl polyethylene glycol phosphate, potassium salt (P-90-481), is subject to reporting under...

  6. 40 CFR 721.3900 - Alkyl polyethylene glycol phosphate, potassium salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkyl polyethylene glycol phosphate... Specific Chemical Substances § 721.3900 Alkyl polyethylene glycol phosphate, potassium salt. (a) Chemical... as alkyl polyethylene glycol phosphate, potassium salt (P-90-481), is subject to reporting under...

  7. 40 CFR 721.3900 - Alkyl polyethylene glycol phosphate, potassium salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl polyethylene glycol phosphate... Specific Chemical Substances § 721.3900 Alkyl polyethylene glycol phosphate, potassium salt. (a) Chemical... as alkyl polyethylene glycol phosphate, potassium salt (P-90-481), is subject to reporting under...

  8. 40 CFR 721.3900 - Alkyl polyethylene glycol phosphate, potassium salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl polyethylene glycol phosphate... Specific Chemical Substances § 721.3900 Alkyl polyethylene glycol phosphate, potassium salt. (a) Chemical... as alkyl polyethylene glycol phosphate, potassium salt (P-90-481), is subject to reporting under...

  9. 40 CFR 721.3900 - Alkyl polyethylene glycol phosphate, potassium salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl polyethylene glycol phosphate... Specific Chemical Substances § 721.3900 Alkyl polyethylene glycol phosphate, potassium salt. (a) Chemical... as alkyl polyethylene glycol phosphate, potassium salt (P-90-481), is subject to reporting under...

  10. The Escherichia coli AlkB protein protects human cells against alkylation-induced toxicity.

    PubMed Central

    Chen, B J; Carroll, P; Samson, L

    1994-01-01

    Escherichia coli can ameliorate the toxic effects of alkylating agents either by preventing DNA alkylation or by repairing DNA alkylation damage. The alkylation-sensitive phenotype of E. coli alkB mutants marks the alkB pathway as an extremely effective defense mechanism against the cytotoxic effects of the SN2, but not the SN1, alkylating agents. Although it is clear that AlkB helps cells to better handle alkylated DNA, no DNA alkylation repair function could be assigned to the purified AlkB protein, suggesting that AlkB either acts as part of a complex or acts to regulate the expression of other genes whose products are directly responsible for alkylation resistance. However, here we present evidence that the provision of alkylation resistance is an intrinsic function of the AlkB protein per se. We expressed the E. coli AlkB protein in two human cell lines and found that it confers the same characteristic alkylation-resistant phenotype in this foreign environment as it does in E. coli. AlkB expression rendered human cells extremely resistant to cell killing by the SN2 but not the SN1 alkylating agents but did not affect the ability of dimethyl sulfate (an SN2 agent) to alkylate the genome. We infer that SN2 agents produce a class of DNA damage that is not efficiently produced by SN1 agents and that AlkB somehow prevents this damage from killing the cell. Images PMID:7928996

  11. 40 CFR 721.10143 - Amines, bis (C11-14-branched and linear alkyl).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... linear alkyl). 721.10143 Section 721.10143 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10143 Amines, bis (C11-14-branched and linear alkyl). (a) Chemical..., bis (C11-14-branched and linear alkyl) (PMN P-06-733; CAS No. 900169-60-0) is subject to...

  12. 40 CFR 721.10143 - Amines, bis (C11-14-branched and linear alkyl).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... linear alkyl). 721.10143 Section 721.10143 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10143 Amines, bis (C11-14-branched and linear alkyl). (a) Chemical..., bis (C11-14-branched and linear alkyl) (PMN P-06-733; CAS No. 900169-60-0) is subject to...

  13. 40 CFR 721.10143 - Amines, bis (C11-14-branched and linear alkyl).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... linear alkyl). 721.10143 Section 721.10143 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10143 Amines, bis (C11-14-branched and linear alkyl). (a) Chemical..., bis (C11-14-branched and linear alkyl) (PMN P-06-733; CAS No. 900169-60-0) is subject to...

  14. 40 CFR 721.10143 - Amines, bis (C11-14-branched and linear alkyl).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... linear alkyl). 721.10143 Section 721.10143 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10143 Amines, bis (C11-14-branched and linear alkyl). (a) Chemical..., bis (C11-14-branched and linear alkyl) (PMN P-06-733; CAS No. 900169-60-0) is subject to...

  15. 40 CFR 721.10143 - Amines, bis (C11-14-branched and linear alkyl).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... linear alkyl). 721.10143 Section 721.10143 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10143 Amines, bis (C11-14-branched and linear alkyl). (a) Chemical..., bis (C11-14-branched and linear alkyl) (PMN P-06-733; CAS No. 900169-60-0) is subject to...

  16. 40 CFR 721.2565 - Alkylated sulfonated diphenyl oxide, alkali and amine salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkylated sulfonated diphenyl oxide... New Uses for Specific Chemical Substances § 721.2565 Alkylated sulfonated diphenyl oxide, alkali and... substances identified as alkylated sulfonated diphenyl oxide, alkali salt (PMN P-93-352) and...

  17. 40 CFR 721.2565 - Alkylated sulfonated diphenyl oxide, alkali and amine salts.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkylated sulfonated diphenyl oxide... New Uses for Specific Chemical Substances § 721.2565 Alkylated sulfonated diphenyl oxide, alkali and... substances identified as alkylated sulfonated diphenyl oxide, alkali salt (PMN P-93-352) and...

  18. 40 CFR 721.644 - Amines, C12-14-tert-alkyl, sulfonates.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Amines, C12-14-tert-alkyl, sulfonates... Substances § 721.644 Amines, C12-14-tert-alkyl, sulfonates. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as amines, C12-14-tert-alkyl, sulfonates...

  19. 40 CFR 721.644 - Amines, C12-14-tert-alkyl, sulfonates.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Amines, C12-14-tert-alkyl, sulfonates... Substances § 721.644 Amines, C12-14-tert-alkyl, sulfonates. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as amines, C12-14-tert-alkyl, sulfonates...

  20. 40 CFR 721.10437 - Sulfonic acid, linear xylene alkylate, mono, sodium salts (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Sulfonic acid, linear xylene alkylate... Significant New Uses for Specific Chemical Substances § 721.10437 Sulfonic acid, linear xylene alkylate, mono... chemical substances identified generically as sulfonic acid, linear xylene alkylate, mono, sodium...

  1. 40 CFR 721.10437 - Sulfonic acid, linear xylene alkylate, mono, sodium salts (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Sulfonic acid, linear xylene alkylate... Significant New Uses for Specific Chemical Substances § 721.10437 Sulfonic acid, linear xylene alkylate, mono... chemical substances identified generically as sulfonic acid, linear xylene alkylate, mono, sodium...

  2. Iridium-catalyzed selective α-alkylation of unactivated amides with primary alcohols.

    PubMed

    Guo, Le; Liu, Yinghua; Yao, Wubing; Leng, Xuebing; Huang, Zheng

    2013-03-01

    The first α-alkylation of unactivated amides with primary alcohols is described. An effective and robust iridium pincer complex has been developed for selective α-alkylation of tertiary and secondary acetamides involving a "borrowing hydrogen" methodology. The method is compatible with alcohols bearing various functional groups. This presents a convenient and environmentally benign protocol for α-alkylation of amides.

  3. 40 CFR 721.10493 - Tris-alkyl-alkoxy melamine polymer (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Tris-alkyl-alkoxy melamine polymer... Specific Chemical Substances § 721.10493 Tris-alkyl-alkoxy melamine polymer (generic). (a) Chemical... as tris-alkyl-alkoxy melamine polymer (PMN P-05-417) is subject to reporting under this section...

  4. 40 CFR 721.10493 - Tris-alkyl-alkoxy melamine polymer (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Tris-alkyl-alkoxy melamine polymer... Specific Chemical Substances § 721.10493 Tris-alkyl-alkoxy melamine polymer (generic). (a) Chemical... as tris-alkyl-alkoxy melamine polymer (PMN P-05-417) is subject to reporting under this section...

  5. 40 CFR 721.5985 - Fatty alkyl phosphate, alkali metal salt (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fatty alkyl phosphate, alkali metal... Specific Chemical Substances § 721.5985 Fatty alkyl phosphate, alkali metal salt (generic). (a) Chemical... as a fatty alkyl phosphate, alkali metal salt (PMN P-99-0385) is subject to reporting under...

  6. 40 CFR 721.5985 - Fatty alkyl phosphate, alkali metal salt (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty alkyl phosphate, alkali metal... Specific Chemical Substances § 721.5985 Fatty alkyl phosphate, alkali metal salt (generic). (a) Chemical... as a fatty alkyl phosphate, alkali metal salt (PMN P-99-0385) is subject to reporting under...

  7. 40 CFR 721.5985 - Fatty alkyl phosphate, alkali metal salt (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fatty alkyl phosphate, alkali metal... Specific Chemical Substances § 721.5985 Fatty alkyl phosphate, alkali metal salt (generic). (a) Chemical... as a fatty alkyl phosphate, alkali metal salt (PMN P-99-0385) is subject to reporting under...

  8. 40 CFR 721.5985 - Fatty alkyl phosphate, alkali metal salt (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty alkyl phosphate, alkali metal... Specific Chemical Substances § 721.5985 Fatty alkyl phosphate, alkali metal salt (generic). (a) Chemical... as a fatty alkyl phosphate, alkali metal salt (PMN P-99-0385) is subject to reporting under...

  9. 40 CFR 721.5985 - Fatty alkyl phosphate, alkali metal salt (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Fatty alkyl phosphate, alkali metal... Specific Chemical Substances § 721.5985 Fatty alkyl phosphate, alkali metal salt (generic). (a) Chemical... as a fatty alkyl phosphate, alkali metal salt (PMN P-99-0385) is subject to reporting under...

  10. Ionic liquid containing hydroxamate and N-alkyl sulfamate ions

    DOEpatents

    Friesen, Cody A.; Wolfe, Derek; Johnson, Paul Bryan

    2016-03-15

    Embodiments of the invention are related to ionic liquids and more specifically to ionic liquids used in electrochemical metal-air cells in which the ionic liquid includes a cation and an anion selected from hydroxamate and/or N-alkyl sulfamate anions.

  11. Microbial degradation of n-alkyl tetrahydrothiophenes found in petroleum.

    PubMed Central

    Fedorak, P M; Payzant, J D; Montgomery, D S; Westlake, D W

    1988-01-01

    Although n-alkyl-substituted tetrahydrothiophenes are found in nonbiodegraded petroleums, they are not found in petroleums which have undergone biodegradation in their reservoirs. These observations suggested that this group of compounds with alkyl chain lengths from approximately C10 to at least C30 is biodegradable. Two of these sulfides, 2-n-dodecyltetrahydrothiophene (DTHT) and 2-n-undecyltetrahydrothiophene, were synthesized, and their biodegradabilities were tested by using five gram-positive, n-alkane-degrading bacterial isolates. The alkyl side chains of these compounds were oxidized, and the major intermediates found in 2-n-undecyltetrahydrothiophene- and DTHT-metabolizing cultures were 2-tetrahydrothiophenecarboxylic acid (THTC) and 2-tetrahydrothiopheneacetic acid (THTA), respectively. Four n-alkane-degrading fungi were also shown to degrade DTHT, yielding both THTA and THTC. Quantitation of tetrahydrothiophene ring-containing products in 28-day-old bacterial and fungal cultures suggested that THTC and THTA were metabolized further to unidentified products. In addition, two of the bacterial isolates were shown to degrade a mixture of n-alkyl tetrahydrothiophenes isolated from Bellshill Lake crude oil. PMID:3389816

  12. On the Boiling Points of the Alkyl Halides.

    ERIC Educational Resources Information Center

    Correia, John

    1988-01-01

    Discusses the variety of explanations in organic chemistry textbooks of a physical property of organic compounds. Focuses on those concepts explaining attractive forces between molecules. Concludes that induction interactions play a major role in alkyl halides and other polar organic molecules and should be given wider exposure in chemistry texts.…

  13. A Green Alternative to Aluminum Chloride Alkylation of Xylene

    ERIC Educational Resources Information Center

    Sereda, Grigoriy A.; Rajpara, Vikul B.

    2007-01-01

    An acutely less toxic 2-bromobutane is used to develop a simple graphite-promoted procedure of alkylation of p-xylene. It is further demonstrated that aluminum chloride is not required, the need for aqueous workup is eliminated, waste solutions are not produced and the multiple use of the catalyst is allowed.

  14. 40 CFR 721.8700 - Halogenated alkyl pyridine.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.8700 Halogenated alkyl pyridine. Link to an amendment published at 79 FR 34638, June 18, 2014. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical...

  15. 40 CFR 721.9720 - Disubstituted alkyl triazines (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.9720 Disubstituted alkyl triazines (generic name). Link to an amendment published at 79 FR 34638, June 18, 2014. (a) Chemical substances and significant new uses subject...

  16. 40 CFR 721.10669 - Tertiary amine alkyl ether (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10669 Tertiary amine alkyl ether (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as tertiary...

  17. Synthesis of hydroxytyrosyl alkyl ethers from olive oil waste waters.

    PubMed

    Madrona, Andrés; Pereira-Caro, Gema; Mateos, Raquel; Rodríguez, Guillermo; Trujillo, Mariana; Fernández-Bolaños, Juan; Espartero, José L

    2009-05-11

    The preparation of a new type of derivatives of the naturally occurring antioxidant hydroxytyrosol is reported. Hydroxytyrosyl alkyl ethers were obtained in high yield by a three-step procedure starting from hydroxytyrosol isolated from olive oil waste waters. Preliminary results obtained by the Rancimat method have shown that these derivatives retain the high protective capacity of free hydroxytyrosol.

  18. Residual Patterns of Alkyl Polyoxyethylene Surfactant Droplets after Water Evaporation

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Using a nonionic, alkyl polyoxyethylene surfactant (X-77®) in aqueous solutions, sessile droplet spreading, pinning, evaporation, contraction, and post-evaporation deposits are characterized. X-77® is widely used in the agricultural field as a spreader/adherent, intended to optimize pathenogenic ag...

  19. Students' understanding of alkyl halide reactions in undergraduate organic chemistry

    NASA Astrophysics Data System (ADS)

    Cruz-Ramirez de Arellano, Daniel

    Organic chemistry is an essential subject for many undergraduate students completing degrees in science, engineering, and pre-professional programs. However, students often struggle with the concepts and skills required to successfully solve organic chemistry exercises. Since alkyl halides are traditionally the first functional group that is studied in undergraduate organic chemistry courses, establishing a robust understanding of the concepts and reactions related to them can be beneficial in assuring students' success in organic chemistry courses. Therefore, the purpose of this study was to elucidate and describe students' understanding of alkyl halide reactions in an undergraduate organic chemistry course. Participants were interviewed using a think-aloud protocol in which they were given a set of exercises dealing with reactions and mechanisms of alkyl halide molecules in order to shed light on the students' understanding of these reactions and elucidate any gaps in understanding and incorrect warrants that may be present. These interviews were transcribed and analyzed using qualitative inquiry approaches. In general, the findings from this study show that the students exhibited gaps in understanding and incorrect warrants dealing with: (1) classifying substances as bases and/or nucleophiles, (2) assessing the basic or nucleophilic strength of substances, (3) accurately describing the electron movement of the steps that take place during alkyl halide reaction mechanisms, and (4) assessing the viability of their proposed reactive intermediates and breakage of covalent bonds. In addition, implications for teaching and future research are proposed.

  20. Students' Understanding of Alkyl Halide Reactions in Undergraduate Organic Chemistry

    ERIC Educational Resources Information Center

    Cruz-Ramirez de Arellano, Daniel

    2013-01-01

    Organic chemistry is an essential subject for many undergraduate students completing degrees in science, engineering, and pre-professional programs. However, students often struggle with the concepts and skills required to successfully solve organic chemistry exercises. Since alkyl halides are traditionally the first functional group that is…

  1. Size Fractionation of Mechanochemical Synthesized Alkyl-Passivated Silicon Nanoparticles

    NASA Astrophysics Data System (ADS)

    Verdoni, Luigi; Mitchell, Brian

    2010-03-01

    A novel top-down procedure was employed for the synthesis of stable alkyl-passivated silicon nanoparticles using reactive high energy ball milling (HEBM) as described in Heintz et al., (Adv. Mater. 2007, 19). The method provides for the simultaneous production of photo luminescent silicon nanoparticles and the passivation of the particle surface with alkyl groups covalently linked through Si-C bonds. As fresh silicon surface is formed during HEBM by particle fracture, the surface Si atoms react in-situ with liquid alkyls, such as 1-octyne and 1-hexyne. We present a multistage size selective fractionation process to isolate and purify initial sample polydispersities ranging from microns down to single nanometers (1 um - 1 nm). This process employs centrifugation, inline nano-filtration, both normal phase gel permission (GPC) and size exclusion chromatography (SEC), followed by recursive size selective precipitation (SSP). Size evolutions of fractions are monitored via UV/VIS absorbance, photoluminescence (PL), and electron microscopy (SEM/TEM). Elemental impurities are quantified through atomic absorption (AAS) and energy dispersive spectroscopy (EDS). Stages are performed in series to isolate and investigate the influence of initial alkyl and silicon reactants on product yields, size dispersity, and optical behavior.

  2. Thermolysis of surface-immobilized phenethyl phenyl ether

    SciTech Connect

    Britt, P.F.; Buchanan, A.C. III; Hitsman, V.M.

    1991-01-01

    Our research has focused on modeling the constraints on free-radical reactions that might be imposed in coal as a consequence of its cross-linked macromolecular structure by covalently bonding diphenylalkanes to an inert silica surface. A surface-immobilized phenethyl phenyl ether ({approx}PhCH{sub 2}CH{sub 2}POh, or {approx}PPE-3) has been prepared as a model for ether linkages in lignin by the condensation of p-HOPhCH{sub 2}CH{sub 2}OPh with the surface hydroxyls of a high purity fumed silica. Thermolysis of {approx}PPE-3 at saturation surface coverage at 375{degree}C produces {approx}PhCH = CH{sub 2} and PhOH as the major products which are consistent with the proposed free-radical chain mechanism for the decomposition of fluid-phase phenethyl phenyl ether. However, significant quantities of {approx}PhCH{sub 3} and PhCHO (ca. 18% of the products) are produced indicating the emergence of a new reaction pathway on the surface. The mechanism for the decomposition of {approx}PPE-3 will be discussed in light of this new information. 18 refs., 1 fig.

  3. Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug.

    PubMed

    Lapin, I

    2001-01-01

    Phenibut (beta-phenyl-gamma-aminobutyric acid HCl) is a neuropsychotropic drug that was discovered and introduced into clinical practice in Russia in the 1960s. It has anxiolytic and nootropic (cognition enhancing) effects. It acts as a GABA-mimetic, primarily at GABA(B) and, to some extent, at GABA(A) receptors. It also stimulates dopamine receptors and antagonizes beta-phenethylamine (PEA), a putative endogenous anxiogenic. The psychopharmacological activity of phenibut is similar to that of baclofen, a p-Cl-derivative of phenibut. This article reviews the structure-activity relationship of phenibut and its derivatives. Emphasis is placed on the importance of the position of the phenyl ring, the role of the carboxyl group, and the activity of optical isomers. Comparison of phenibut with piracetam and diazepam reveals similarities and differences in their pharmacological and clinical effects. Phenibut is widely used in Russia to relieve tension, anxiety, and fear, to improve sleep in psychosomatic or neurotic patients; as well as a pre- or post-operative medication. It is also used in the therapy of disorders characterized by asthenia and depression, as well as in post-traumatic stress, stuttering and vestibular disorders.

  4. 6-Butyryl-5-hy-droxy-4-phenyl-seselin.

    PubMed

    Aree, Thammarat; Tip-Pyang, Santi; Sowanthip, Preecha

    2010-08-28

    IN THE TITLE COUMARIN COMPOUND (SYSTEMATIC NAME: 6-butyryl-5-hy-droxy-8,8-dimethyl-4-phenyl-2H,8H-benzo[1,2-b;3,4-b']dipyran-2-one), C(24)H(22)O(5), also known as mammea A/AC cyclo D, the chromene and pyran rings are almost coplanar with a maximum deviation from the mean plane of 0.295 (2) Å. The attached phenyl group is inclined at 53.49 (8)° with respect to the chromene ring. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are linked into sheets parallel to (101) by inter-molecular C-H⋯O hydrogen bonds. Adjacent sheets are sustained by inter-molecular C-H⋯π and π-π [centroid-centroid distance = 4.471 (2) Å] inter-actions.

  5. Aerobic oxidative cyclization of benzamides via meta-selective C-H tert-alkylation: rapid entry to 7-alkylated isoquinolinediones.

    PubMed

    Tang, Shi; Deng, You-Lin; Li, Jie; Wang, Wen-Xin; Wang, Ying-Chun; Li, Zeng-Zeng; Yuan, Li; Chen, Shi-Lu; Sheng, Rui-Long

    2016-03-25

    A novel copper-catalyzed aerobic oxidative cyclization of benzamides via meta-selective C-H tert-alkylation using AIBN and analogues as radical precursors was described. This strategy provides an elusive and rapid means to 7-tert-alkylated isoquinolinediones, as well as the construction of tertiary alkyl-aryl C(sp(3))-C(sp(2)) bonds with positional selectivity.

  6. Preparation and evaluation of radioiodinated 1-methyl-1-(alkyl or hydroxyalkyl)-4-phenylpiperazinium salts as myocardial imaging agents

    SciTech Connect

    Hanson, R.N.; Hassan, M.A.

    1985-05-01

    In this study the authors evaluate the effect of various substituents upon the myocardial uptake and selectivity of radioiodinated phenylpiperazinium derivatives. A series of 1-methyl-1-(alkyl or hydroxyalkyl)-4-(substituted phenyl) piperazinium salts were synthesized, characterized, radioiodinated at the no-carrier-added level with Na/sup 125/I and chloroamine-T, and isolated in 50-85% radiochemical yields using HPLC. The tissue distribution of the radiochemicals was determined in rats at 0.25 - 4 hr following i.v. administration. The compounds where R/sub 2/=CH/sub 2/CH/sub 2/OH had the highest myocardial uptake and selectivity. The radioactivity in the heart did not diminish during the time period evaluation but also was not displaced by tetraethylammonium, or other quaternary amines. Scintigraphic imaging in the dog with (I-131) 1-methyl-1-(2-hydroxyethyl)-4-(2-methylphenyl)piperazine clearly visualized the heart. Following sacrifice at 2 hrs and tissue dissection, the heart uptake was 4.5-6.5% ID with H/B1=25 and H/lung=l.5. In summary, the initial data suggest that this agent which can be readily labeled with radioiodide possesses substantial potential as a myocardial perfusion agent.

  7. Levels and pattern of alkyl nitrates, multifunctional alkyl nitrates, and halocarbons in the air over the Atlantic Ocean

    NASA Astrophysics Data System (ADS)

    Fischer, Ralf G.; Kastler, Jürgen; Ballschmiter, Karlheinz

    2000-06-01

    The Albatross Campaign was a research cruise of the German research vessel RV Polarstern (cruise ANT XFV/1) in October and November 1996 across the Atlantic Ocean. The cruise started in Bremerhaven, Germany, reached the polar region at 67°N, followed the 30°W meridian longitude, crossed the equatorial region, and ended at 50°S at Punta Quilla, Argentina. A second cruise leg closer to the African continent started from Capetown, South Africa, passed the Canary Island, and ended through the English Channel at Bremerhaven, Germany, in May/June 1998. Measurements of atmospheric levels of C1-C13 alkyl mononitrates, 24 alkyl dinitrates (C3-C6), 19 hydroxy alkyl nitrates (C2-C6), and benzyl nitrate, as well as the halocarbons tetrachloroethene, hexachloroethane, and bromoform are presented in this work. The halocarbons are used to assess the origin of the air parcels analyzed. Levels and patterns of multifunctional alkyl nitrates in the marine air are described here for the first time. The air masses include polluted air from the northern Europe, as well as highly degraded air masses of the South Atlantic trade wind region that represent global baseline levels. Two independent analytical methods were used in combination to cover the whole range of organic nitrates. First, the low-volume adsorptive enrichment of organic traces on Tenax, followed by thermodesorption cold trap HRGC-ECD and thermodesorption cold trap HRGC-(EI)MSD was used. Second, high-volume adsorptive enrichment of organic traces on silica gel was applied followed by solvent desorption, NP-HPLC group separation, and HRGC-(EI)-MSD. Short-chain alkyl nitrates (C4-C6) showed mixing ratios in the range of 0.2-2.5 parts per trillion by volume (pptv), with a local minimum for the tropical regions and significantly lower ratios for the Southern Hemisphere. The mixing ratio of the sum of 36 long-chain alkyl mononitrates (C7-C13) ranged from 0.02-0.43 pptv, the mixing ratio of the sum of 23 alkyl dinitrates (C3-C

  8. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  9. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  10. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  11. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  12. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  13. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  14. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  15. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  16. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  17. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  18. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  19. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  20. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  1. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  2. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  3. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  4. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  5. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  6. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  7. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  8. Synthesis, antitubercular, antifungal and antibacterial activities of 6-substituted phenyl-2-(3'-substituted phenyl pyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-one.

    PubMed

    Islam, Mojahidul; Siddiqui, Anees A; Rajesh, Ramadoss

    2008-01-01

    A series of 6-substituted phenyl-2-(3'-substituted phenyl pyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-ones has been synthesized. An appropriate aromatic hydrocarbon reacts with succinic anhydride in presence of AlCl3 to yield beta-aroyl propionic acid. The corresponding acid was cyclized with hydrazine hydrate to give 6-(substituted aryl)-2,3,4,5-tetrahydro-3-pyridazinone, which was heated on steam bath with phosphorus(V) oxychloride to yield 3-chloro 6-substituted phenyl pyridazine. This intermediate after reaction with hydrazine hydrate was converted into 3-hydrazino-6-substituted phenyl pyridazine. The resulting product was converted into 6-substituted phenyl-2-(3'-substituted phenyl pyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-one by reacting with substituted aroyl propionic acid. Spectral data (IR, NMR, mass spectra) confirmed the structures of the synthesized compounds. The synthesized compounds were investigated for their in vitro antitubercular, antifungal and antibacterial activities. The results indicated that the synthesized compounds have mild to potent activities with reference to their appropriate reference standards.

  9. Inhibitory Activities of Alkyl Syringates and Related Compounds on Aflatoxin Production

    PubMed Central

    Furukawa, Tomohiro; Iimura, Kurin; Kimura, Taichi; Yamamoto, Toshiyoshi; Sakuda, Shohei

    2016-01-01

    Inhibitors of aflatoxin production of aflatoxigenic fungi are useful for preventing aflatoxin contamination in crops. As methyl syringate weakly inhibits aflatoxin production, aflatoxin production inhibitory activities of additional alkyl syringates with alkyl chains from ethyl to octyl were examined. Inhibitory activity toward aflatoxin production of Aspergillus flavus became stronger as the length of the alkyl chains on the esters became longer. Pentyl, hexyl, heptyl, and octyl syringates showed strong activity at 0.05 mM. Heptyl and octyl parabens, and octyl gallate also inhibited aflatoxin production as strongly as octyl syringate. Alkyl parabens and alkyl gallates inhibit the complex II activity of the mitochondrial respiration chain; thus, whether alkyl syringates inhibit complex II activity was examined. Inhibitory activities of alkyl syringates toward complex II also became stronger as the length of the alkyl chains increased. The complex II inhibitory activity of octyl syringate was comparable to that of octyl paraben and octyl gallate. These results suggest that alkyl syringates, alkyl parabens, and alkyl gallates, including commonly used food additives, are useful for aflatoxin control. PMID:27338472

  10. Enhanced biological activity of carotenoids stabilized by phenyl groups.

    PubMed

    You, Ji Suk; Jeon, Sunhwa; Byun, Youn Jung; Koo, Sangho; Choi, Shin Sik

    2015-06-15

    Carotenoids are lipid soluble food ingredients with multifunction including antioxidant and anticancer activities. However, carotenoids are destructively oxidized upon reaction with radicals resulting in toxic effects on biological systems. Two synthetic carotenoids (BAS and BTS) containing the aromatic phenyl groups with a para-substituent (OMe and Me, respectively) at C-13 and C-13' position were prepared in order to overcome a structural instability of carotenoid. Both BAS and BTS exerted stronger radical scavenging activity than β-carotene in DPPH and ABTS assays. In particular, BTS significantly reduced in vivo ROS (reactive oxygen species) levels and improved body growth and reproduction of Caenorhabditiselegans. BTS has a great potential for the advanced and modified carotenoid material with stability leading to enhanced bioavailability.

  11. Novel nonsecosteroidal VDR agonists with phenyl-pyrrolyl pentane skeleton.

    PubMed

    Shen, Wei; Xue, Jingwei; Zhao, Zekai; Zhang, Can

    2013-11-01

    In order to find the vitamin D receptor (VDR) ligand whose VDR agonistic activity is separated from the calcemic activity sufficiently, novel nonsecosteroidal analogs with phenyl-pyrrolyl pentane skeleton were synthesized and evaluated for the VDR binding affinity, antiproliferative activity in vitro and serum calcium raising ability in vivo (tacalcitol used as control). Among them, several compounds showed varying degrees of VDR agonistic and growth inhibition activities of the tested cell lines. The most effective compound 2g (EC₅₀: 1.06 nM) exhibited stronger VDR agonistic activity than tacalcitol (EC₅₀: 7.05 nM), inhibited the proliferations of HaCaT and MCF-7 cells with IC₅₀ of 2.06 μM and 0.307 μM (tacalcitol: 2.07 μM and 0.057 μM) and showed no significant effect on serum calcium.

  12. Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.

    PubMed

    Fobofou, Serge Alain Tanemossu; Harmon, Chelsea Rebecca; Lonfouo, Antoine Honoré Nkuete; Franke, Katrin; Wright, Stephen M; Wessjohann, Ludger A

    2016-04-01

    In search for new or chemo-taxonomically relevant bioactive compounds from chemically unexplored Hypericum species, four previously undescribed natural products, named peplidiforones A-D were isolated and characterized from Hypericum peplidifolium A. Rich., together with six known compounds. The structures of all compounds were elucidated by extensive 1D- and 2D-NMR experiments, high resolution mass spectrometric analyses (HR-MS), and by comparison with data reported in the literature. Seven of these compounds are phenyl polyketides while three are acylphloroglucinol type compounds. Peplidiforone C, which possesses an unusual carbon skeleton consisting of a furan ring substituted by a 2,2-dimethylbut-3-enoyl moiety, is the first example of a prenylated furan derivative isolated from the genus Hypericum. The cytotoxicity, antifungal, and anti-herpes simplex virus type 1 (HSV-1) activities of extracts and compounds are described.

  13. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  14. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  15. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  16. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  17. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  18. 40 CFR 721.10409 - Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl)oxy]carbonyl] amino]phenyl]amino...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ....- carbonyl] amino]phenyl]amino]carbonyl]- .omega.-methoxy-(generic). 721.10409 Section 721.10409 Protection...(oxyalkylenediyl), .alpha.- carbonyl] amino]phenyl]amino]carbonyl]- .omega.-methoxy-(generic). (a) Chemical... as poly(oxyalkylenediyl), .alpha.- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (PMN...

  19. 40 CFR 721.10409 - Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl) oxy]carbonyl]amino]phenyl]amino...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ....- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (generic). 721.10409 Section 721.10409 Protection...(oxyalkylenediyl), .alpha.- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (generic). (a) Chemical... as poly(oxyalkylenediyl), .alpha.- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (PMN...

  20. Activity of quinone alkylating agents in quinone-resistant cells.

    PubMed

    Begleiter, A; Leith, M K

    1990-05-15

    The role of the quinone group in the antitumor activity of quinone alkylating agents, such as mitomycin C and 2,5-diaziridinyl-3,5-bis(carboethoxyamino)-1,4-benzoquinone, is still uncertain. The quinone group may contribute to antitumor activity by inducing DNA strand breaks through the formation of free radicals and/or by influencing the alkylating activity of the quinone alkylators. The cytotoxic activity and DNA damage produced by the model quinone alkylating agents, benzoquinone mustard and benzoquinone dimustard, were compared in L5178Y murine lymphoblasts sensitive and resistant to the model quinone antitumor agent, hydrolyzed benzoquinone mustard. The resistant cell lines, L5178Y/HBM2 and L5178Y/HBM10, have increased concentrations of glutathione and elevated catalase, superoxide dismutase, glutathione S-transferase, and DT-diaphorase activity. L5178Y/HBM2 and L5178Y/HBM10 cells were 7.4- and 8.5-fold less sensitive to benzoquinone mustard and 1.7- and 4.3-fold less sensitive to benzoquinone dimustard, respectively, compared with sensitive cells, but showed no resistance to the non-quinone alkylating agent, aniline mustard. The formation of DNA double strand breaks by benzoquinone mustard was reduced by 2- and 8-fold in L5178Y/HBM2 and L5178Y/HBM10 cells, respectively, while double strand break formation by benzoquinone dimustard was reduced only in the L5178Y/HBM10 cells. The number of DNA-DNA cross-links produced by benzoquinone mustard was 3- and 6-fold lower, and the number produced by benzoquinone dimustard was 35% and 2-fold lower in L5178Y/HBM2 and L5178Y/HBM10 cells, respectively, compared with L5178Y parental cells. In contrast, cross-linking by aniline mustard was unchanged in sensitive and resistant cells. Dicoumarol, an inhibitor of DT-diaphorase, increased the cytotoxic activity of both benzoquinone mustard and benzoquinone dimustard in L5178Y/HBM10 cells. This study provides evidence that elevated DT-diaphorase activity in the resistant cells

  1. Method for reactivating solid catalysts used in alkylation reactions

    DOEpatents

    Ginosar, Daniel M.; Thompson, David N.; Coates, Kyle; Zalewski, David J.; Fox, Robert V.

    2003-06-17

    A method for reactivating a solid alkylation catalyst is provided which can be performed within a reactor that contains the alkylation catalyst or outside the reactor. Effective catalyst reactivation is achieved whether the catalyst is completely deactivated or partially deactivated. A fluid reactivating agent is employed to dissolve catalyst fouling agents and also to react with such agents and carry away the reaction products. The deactivated catalyst is contacted with the fluid reactivating agent under pressure and temperature conditions such that the fluid reactivating agent is dense enough to effectively dissolve the fouling agents and any reaction products of the fouling agents and the reactivating agent. Useful pressures and temperatures for reactivation include near-critical, critical, and supercritical pressures and temperatures for the reactivating agent. The fluid reactivating agent can include, for example, a branched paraffin containing at least one tertiary carbon atom, or a compound that can be isomerized to a molecule containing at least one tertiary carbon atom.

  2. Bacteria-driven production of alkyl nitrates in seawater

    NASA Astrophysics Data System (ADS)

    Kim, Michelle J.; Michaud, Jennifer M.; Williams, Renee; Sherwood, Byron Pedler; Pomeroy, Robert; Azam, Farooq; Burkart, Michael; Bertram, Timothy H.

    2015-01-01

    and ship-borne measurements have shown that the ocean is a large, diffuse source for short chain (C1-C3) gas phase alkyl nitrates (RONO2). Photochemical production of RONO2 has been demonstrated previously as a viable mechanism in surface waters; however, it cannot account for the observed depth profile of RONO2, suggesting an additional, dark RONO2 production mechanism. We present measurements of gas phase C1-C5 alkyl nitrates emitted from seawater in a controlled mesocosm experiment conducted under low-light conditions in a glass-walled wave channel. Ethyl and butyl nitrate emission rates from seawater are strongly correlated with the abundance of heterotrophic bacteria (R2 ≥ 0.89) and show no correlation to chlorophyll a concentration. Controlled flask experiments conducted using ambient and sterile seawater, inoculated with a heterotrophic bacterium, confirm that bacterial driven production of select RONO2 can proceed efficiently in the absence of light.

  3. The Effect of Supercritical Fluids on Solid Acid Catalyst Alkylation

    SciTech Connect

    Ginosar, Daniel Michael; Thompson, David Neil; Burch, Kyle Coates; Zalewski, D. J.

    2002-05-01

    The alkylation of isobutane with trans-2-butene was explored over six solid acid catalysts in the liquid, near-critical liquid, and supercritical regions through the addition of an inert cosolvent to the reaction feed mixture. The addition of supercritical cosolvents did not result in sustained catalytic alkylation activity. A modest improvement in product yield was obtained with the addition of methane in the modified-liquid region; however, catalyst longevity and product selectivity were decreased compared to cosolvent-free liquid conditions. This paper describes the catalyst screening and selection process, an exploration of catalyst performance with varying concentrations of methane, and an examination of the effects of seven supercritical fluids on catalyst performance. The catalysts included two zeolites, two sulfated metal oxides, and two Nafion catalysts. Three hydrocarbons, two fluorocarbons, carbon dioxide, and sulfur hexafluoride were explored as inert cosolvents added to the reaction mixture.

  4. Safety Assessment of Alkyl Esters as Used in Cosmetics.

    PubMed

    Fiume, Monice M; Heldreth, Bart A; Bergfeld, Wilma F; Belsito, Donald V; Hill, Ronald A; Klaassen, Curtis D; Liebler, Daniel C; Marks, James G; Shank, Ronald C; Slaga, Thomas J; Snyder, Paul W; Andersen, F Alan

    2015-09-01

    The Cosmetic Ingredient Review Expert Panel (Panel) assessed the safety of 237 alkyl esters for use in cosmetics. The alkyl esters included in this assessment have a variety of reported functions in cosmetics, with skin-conditioning agent being the most common function. The Panel reviewed available animal and clinical data in making its determination of safety on these ingredients, and where there were data gaps, similarity in structure, properties, functions, and uses of these ingredients allowed for extrapolation of the available toxicological data to assess the safety of the entire group. The Panel concluded that these ingredients are safe in cosmetic formulations in the present practices of use and concentration when formulated to be nonirritating.

  5. Metabolism of alkyl amines by the filamentous fungus Aspergillus versicolor.

    PubMed Central

    Lindley, N D

    1987-01-01

    A variety of monoalkyl-substituted amines were able to act as nitrogen sources for heterotrophically growing cultures of Aspergillus versicolor. Only amines whose alkyl chains were at least five carbon atoms long were capable of supporting significant growth in the absence of a separate carbon substrate. However, biomass yields were significantly higher during growth on glucose-amine than on glucose-ammonia, indicating that some energy-generating dissimilation of the amine to CO2 took place. PMID:3566265

  6. Cold-surface photochemistry of primary and tertiary alkyl nitrites.

    PubMed

    McLaughlin, Ryan P; O'Sullivan, Daniel; Sodeau, John R

    2012-06-28

    Reflection-absorption infrared spectroscopy (RAIRS) is used to explore the photochemistry of primary and tertiary alkyl nitrites deposited on a gold surface. The primary alkyl nitrites examined for this study were n-butyl, isobutyl, and isopentyl nitrite. These compounds showed qualitatively similar spectra to those observed in previous condensed-phase measurements. The photolysis of the primary nitrites involved the initial formation of an alkoxy radical and NO, followed by production of nitroxyl (HNO) and an aldehydic species. In addition, the formation of nitrous oxide, identified from its distinctive transition near 2230 cm(-1), was observed to form from the self-reaction of nitroxyl. The reaction rates for cis and trans conformer decay, as tracked through their intense N═O stretching modes, were found to be significantly different, potentially due to a structural bias that favors HNO formation for the initial trans conformer photoproducts over recombination. Tert-butyl nitrite demonstrates only the trans conformer in the RAIRS spectra prior to photolysis; however, recombination of the initial NO and RO(•) photoproducts was observed to produce the cis conformer in the photolyzed samples. The primary photoproducts from tert-butyl nitrite can also react to form acetone and nitrosomethane, but the absence of HNO prohibits the formation of N(2)O that was observed for the primary alkyl nitrites. Additionally, the RAIRS spectrum of isobutyl nitrite co-deposited with water was measured to examine the photolysis of this species on a water-ice surface. No change in the identity of the photoproducts was observed in this experiment, and minimal frequency shifting (1-3 cm(-1)) of the vibrational modes occurred. In addition to being a known atmospheric source of NO and various aldehydes, our results point to cold surface processing of alkyl nitrites as a potential environmental source of nitrous oxide.

  7. Alkylation of lignites and peat in low-temperature plasma

    SciTech Connect

    L.I. Shchukin; S.I. Zherebtsov; M.V. Kornievich; O.A. Skutina

    2007-02-15

    The alkylation of lignites and peat was carried out at 50-270{sup o}C in different plasmas. The degree of conversion determined as the yield of the alcohol-benzene extract increases on passing from methane to alcohol plasma. The dependence of the extract yield on the plasma temperature, treatment time, and sample grinding degree was studied. 5 refs., 4 figs., 2 tabs.

  8. New potential of the reductive alkylation of amines

    NASA Astrophysics Data System (ADS)

    Gusak, K. N.; Ignatovich, Zh V.; Koroleva, E. V.

    2015-03-01

    Available data on the reductive alkylation of amines with carbonyl compounds — a key method for the preparation of secondary and tertiary amines — are described systematically. The review provides information on the relevant reducing agents and catalysts and on the use of chiral catalysts in stereo- and enantiocontrolled reactions of amine synthesis. The effect of the reactant and catalyst structures on the reaction rates and chemo- and stereo(enantio)selectivity is considered. The bibliography includes 156 references.

  9. Alkyl nitrate photochemistry during the tropospheric organic chemistry experiment

    NASA Astrophysics Data System (ADS)

    Worton, David R.; Reeves, Claire E.; Penkett, Stuart A.; Sturges, William T.; Slemr, Jana; Oram, David E.; Bandy, Brian J.; Bloss, William J.; Carslaw, Nicola; Davey, James; Emmerson, Kathryn M.; Gravestock, Thomas J.; Hamilton, Jacqueline F.; Heard, Dwayne E.; Hopkins, James R.; Hulse, Anne; Ingram, Trevor; Jacob, Mark J.; Lee, James D.; Leigh, Roland J.; Lewis, Alastair C.; Monks, Paul S.; Smith, Shona C.

    2010-02-01

    Alkyl nitrates (C 1-C 5) were measured at two sites (near urban and rural) in southeast England during the Tropospheric Organic Chemistry Experiment (TORCH). Methyl nitrate was the dominant species during both campaigns accounting for on average about one third of the total measured alkyl nitrates. High mixing ratios (>50 pptv) and variability of methyl nitrate were observed at the near urban site (TORCH1) that were not seen at the rural site (TORCH2) and which could not be explained by local photochemical production or direct emissions. The diurnal variation of methyl nitrate during TORCH1 showed a morning maximum that would be consistent with nighttime chemistry followed by transport to the surface by boundary layer dynamics. Similarly, elevated morning mixing ratios were also observed during TORCH2 although the magnitudes were much smaller. As a result, methyl nitrate could represent a tracer for nighttime chemistry seen at the ground the following day. At both campaigns, the dominant source of short chain alkyl nitrates and carbonyl precursor radicals (≤C 4) were from decomposition of larger compounds. The magnitude of the source increased with decreasing carbon number consistent with increasing total precursor abundance. Non-photochemical emissions of acetaldehyde and acetone could not be accounted for by automobile exhaust emissions alone and indicated that other direct sources are likely important in this environment.

  10. Separation and quantitative analysis of alkyl sulfate ethoxymers by HPLC.

    PubMed

    Morvan, Julien; Hubert-Roux, Marie; Agasse, Valérie; Cardinael, Pascal; Barbot, Florence; Decock, Gautier; Bouillon, Jean-Philippe

    2008-01-01

    Separation of alkyl sulfate ethoxymers is investigated on various high-performance liquid chromatography (HPLC) stationary phases: Acclaim C18 Surfactant, Surfactant C8, and Hypercarb. For a fixed alkyl chain length, ethoxymers are eluted in the order of increasing number of ethoxylated units on Acclaim C18 Surfactant, whereas a reversed elution order is observed on Surfactant C8 and Hypercarb. Moreover, on an Acclaim C18 Surfactant column, non-ethoxylated compounds are eluted in their ethoxymers distribution and the use of sodium acetate additive in mobile phase leads to a co-elution of ethoxymers. HPLC stationary phases dedicated to surfactants analysis are evaluated by means of the Tanaka test. Surfactant C8 presents a great silanol activity whereas Acclaim C18 Surfactant shows a high steric selectivity. For alkyl sulfates, linearity of the calibration curve and limits of detection and quantitation are evaluated. The amount of sodium laureth sulfate raw material found in commercial body product is in agreement with the specification of the manufacturer.

  11. Chemotherapy-induced pulmonary hypertension: role of alkylating agents.

    PubMed

    Ranchoux, Benoît; Günther, Sven; Quarck, Rozenn; Chaumais, Marie-Camille; Dorfmüller, Peter; Antigny, Fabrice; Dumas, Sébastien J; Raymond, Nicolas; Lau, Edmund; Savale, Laurent; Jaïs, Xavier; Sitbon, Olivier; Simonneau, Gérald; Stenmark, Kurt; Cohen-Kaminsky, Sylvia; Humbert, Marc; Montani, David; Perros, Frédéric

    2015-02-01

    Pulmonary veno-occlusive disease (PVOD) is an uncommon form of pulmonary hypertension (PH) characterized by progressive obstruction of small pulmonary veins and a dismal prognosis. Limited case series have reported a possible association between different chemotherapeutic agents and PVOD. We evaluated the relationship between chemotherapeutic agents and PVOD. Cases of chemotherapy-induced PVOD from the French PH network and literature were reviewed. Consequences of chemotherapy exposure on the pulmonary vasculature and hemodynamics were investigated in three different animal models (mouse, rat, and rabbit). Thirty-seven cases of chemotherapy-associated PVOD were identified in the French PH network and systematic literature analysis. Exposure to alkylating agents was observed in 83.8% of cases, mostly represented by cyclophosphamide (43.2%). In three different animal models, cyclophosphamide was able to induce PH on the basis of hemodynamic, morphological, and biological parameters. In these models, histopathological assessment confirmed significant pulmonary venous involvement highly suggestive of PVOD. Together, clinical data and animal models demonstrated a plausible cause-effect relationship between alkylating agents and PVOD. Clinicians should be aware of this uncommon, but severe, pulmonary vascular complication of alkylating agents.

  12. Synthesis and Antioxidant Activity of Hydroxytyrosol Alkyl-Carbonate Derivatives.

    PubMed

    Fernandez-Pastor, Ignacio; Fernandez-Hernandez, Antonia; Rivas, Francisco; Martinez, Antonio; Garcia-Granados, Andres; Parra, Andres

    2016-07-22

    Three procedures have been investigated for the isolation of tyrosol (1) and hydroxytyrosol (2) from a phenolic extract obtained from the solid residue of olive milling. These three methods, which facilitated the recovery of these phenols, were chemical or enzymatic acetylation, benzylation, and carbomethoxylation, and subsequent carbonylation or acetonation reactions. Several new lipophilic alkyl-carbonate derivatives of hydroxytyrosol have been synthesized, coupling the primary hydroxy group of this phenol, through a carbonate linker, using alcohols with different chain lengths. The antioxidant properties of these lipophilic derivatives have been evaluated by different methods and compared with free hydroxytyrosol (2) and also with the well-known antioxidants BHT and α-tocopherol. Three methods were used for the determination of this antioxidant activity: FRAP and ABTS assays, to test the antioxidant power in hydrophilic media, and the Rancimat test, to evaluate the antioxidant capacity in a lipophilic matrix. These new alkyl-carbonate derivatives of hydroxytyrosol enhanced the antioxidant activity of this natural phenol, with their antioxidant properties also being higher than those of the commercial antioxidants BHT and α-tocopherol. There was no clear influence of the side-chain length on the antioxidant properties of the alkyl-carbonate derivatives of 2, although the best results were achieved mainly by the compounds with a longer chain on the primary hydroxy group of this natural phenolic substance.

  13. Complete assignment of NMR data of 22 phenyl-1H-pyrazoles' derivatives.

    PubMed

    de Oliveira, Aline Lima; Alves de Oliveira, Carlos Henrique; Mairink, Laura Maia; Pazini, Francine; Menegatti, Ricardo; Lião, Luciano Morais

    2011-08-01

    Complete assignment of (1)H and (13)C NMR chemical shifts and J((1)H/(1)H and (1)H/(19)F) coupling constants for 22 1-phenyl-1H-pyrazoles' derivates were performed using the concerted application of (1)H 1D and (1)H, (13)C 2D gs-HSQC and gs-HMBC experiments. All 1-phenyl-1H-pyrazoles' derivatives were synthesized as described by Finar and co-workers. The formylated 1-phenyl-1H-pyrazoles' derivatives were performed under Duff's conditions.

  14. Noncanonical regulation of alkylation damage resistance by the OTUD4 deubiquitinase

    PubMed Central

    Zhao, Yu; Majid, Mona C; Soll, Jennifer M; Brickner, Joshua R; Dango, Sebastian; Mosammaparast, Nima

    2015-01-01

    Repair of DNA alkylation damage is critical for genomic stability and involves multiple conserved enzymatic pathways. Alkylation damage resistance, which is critical in cancer chemotherapy, depends on the overexpression of alkylation repair proteins. However, the mechanisms responsible for this upregulation are unknown. Here, we show that an OTU domain deubiquitinase, OTUD4, is a positive regulator of ALKBH2 and ALKBH3, two DNA demethylases critical for alkylation repair. Remarkably, we find that OTUD4 catalytic activity is completely dispensable for this function. Rather, OTUD4 is a scaffold for USP7 and USP9X, two deubiquitinases that act directly on the AlkB proteins. Moreover, we show that loss of OTUD4, USP7, or USP9X in tumor cells makes them significantly more sensitive to alkylating agents. Taken together, this work reveals a novel, noncanonical mechanism by which an OTU family deubiquitinase regulates its substrates, and provides multiple new targets for alkylation chemotherapy sensitization of tumors. PMID:25944111

  15. Alkyl and Aromatic Amines as Digestive Ripening/Size Focusing Agents for Gold Nanoparticles

    PubMed Central

    Sun, Yijun; Jose, Deepa; Sorensen, Christopher; Klabunde, Kenneth J.

    2013-01-01

    Both long chain alkyl thiols and alkyl amines behave as size focusing agents for gold nanoparticles, a process that is under thermodynamic control. However, amines do not oxidize surface gold atoms while thiols do oxidize surface gold to gold(I) with evolution of hydrogen gas. Therefore, alkyl amines participate in digestive ripening by a different mechanism. The efficiency of alkyl amines for this process is described and compared, and ultimate gold particle size differences are discussed. Reported herein is a detailed investigation of alkyl chain lengths for alkyl amines, aromatic amines (aniline), and unusually reactive amines (2-phenylethyl amine). Also, two methods of preparation of the crude gold nanoparticles were employed: gold ion reduction/inverse micelle vs. metal vaporization (Solvated Metal Atom Dispersion—SMAD).

  16. Solid-acid alkylation process development is at a crucial stage

    SciTech Connect

    Rao, P.; Vatcha, S.R.

    1996-09-09

    The refining industry is seeking more environmentally acceptable and economical methods of producing reformulated gasoline (RFG). Alkylate, the cleanest gasoline-blending stream produced in a refinery, is a prime blend stock for RFG production. Alkylation with solid acid catalysts has potential environmental and safety advantages over conventional liquid-acid alkylation. This is especially true for the HF alkylation process. Difficult technical challenges must be overcome in the next few years to achieve a commercially successful solid-acid alylation process. Substantial innovations in catalysts, catalyst regeneration, reactor design, and product separation will be required for solid catalyst processes to replace the incumbent processes, which are being improved continually. The paper discusses background, HF alkylation, H{sub 2}SO{sub 4} alkylation, solid-acid catalysts, reaction mechanism, activity and selectivity, feedstock effects, catalyst life, resistance to poisons, reactors and processes, business issues, and R and D guidelines.

  17. Noncanonical regulation of alkylation damage resistance by the OTUD4 deubiquitinase.

    PubMed

    Zhao, Yu; Majid, Mona C; Soll, Jennifer M; Brickner, Joshua R; Dango, Sebastian; Mosammaparast, Nima

    2015-06-12

    Repair of DNA alkylation damage is critical for genomic stability and involves multiple conserved enzymatic pathways. Alkylation damage resistance, which is critical in cancer chemotherapy, depends on the overexpression of alkylation repair proteins. However, the mechanisms responsible for this upregulation are unknown. Here, we show that an OTU domain deubiquitinase, OTUD4, is a positive regulator of ALKBH2 and ALKBH3, two DNA demethylases critical for alkylation repair. Remarkably, we find that OTUD4 catalytic activity is completely dispensable for this function. Rather, OTUD4 is a scaffold for USP7 and USP9X, two deubiquitinases that act directly on the AlkB proteins. Moreover, we show that loss of OTUD4, USP7, or USP9X in tumor cells makes them significantly more sensitive to alkylating agents. Taken together, this work reveals a novel, noncanonical mechanism by which an OTU family deubiquitinase regulates its substrates, and provides multiple new targets for alkylation chemotherapy sensitization of tumors.

  18. Low-risk gasoline alkylation process using a homogeneous liquid phase catalyst

    SciTech Connect

    Nelson, S.R.; Nelson, L.G.

    1996-12-31

    Kerr-McGee`s interest in finding additional applications for its ROSES technology has led to a promising new alkylation process for the production of gasoline. The technology is timely due to its inherent environmental safety. The Homogeneous Alkylation Technology (HAT{trademark}) process uses a soluble alkylaluminum chloride-based catalyst at less than 1 percent of the acid concentrations used in conventional alkylation processes. The patented process greatly reduces the environmental risks associated with accidental acid releases from HF and sulfuric acid alkylation units. In addition, the process is projected to operate at lower cost than sulfuric acid alkylation and is a retrofit option for existing HF and sulfuric-acid alkylation units. Kerr-McGee has entered into a relationship with a major U.S. refiner to carry on the development of the HAT process. A gallon-per-day-scale pilot unit has been constructed for use in developing the process. 1 fig., 1 tab.

  19. Facile C-H alkylation in water: enabling defect-free materials for optoelectronic devices.

    PubMed

    Saikia, Gunin; Iyer, Parameswar K

    2010-04-16

    A facile method for the alkylation of fluorene achieved via direct C-H alkylation under aqueous conditions is reported, wherein the formation of fluorenone is inhibited, resulting in the exclusive formation of the desired dialkyl-substituted fluorene monomer. As a proof of concept, this method has also been successfully extended to perform N-alkylation of carbazole, diphenylamine, and N,N-dialkylation of aniline in high yields.

  20. Copper-catalyzed intermolecular carboetherification of unactivated alkenes by alkyl nitriles and alcohols.

    PubMed

    Chatalova-Sazepin, Claire; Wang, Qian; Sammis, Glenn M; Zhu, Jieping

    2015-04-27

    A three-component carboetherification of unactivated alkenes has been developed allowing the rapid building of complexity from simple starting materials. A wide range of α-substituted styrenes underwent smooth reactions with unactivated alkyl nitriles and alcohols to afford γ-alkoxy alkyl nitriles with concomitant generation of a quaternary carbon center. A radical clock experiment provided clear-cut evidence that the reaction proceeds through a tertiary alkyl radical intermediate.

  1. Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems

    PubMed Central

    2015-01-01

    Summary Recently, a number of papers have emerged demonstrating copper-catalyzed alkylation reactions of electron-rich small molecules. The processes are generally thought to be related to long established atom-transfer radical reactions. However, unlike classical reactions, these new transformations lead to simple alkylation products. This short review will highlight recent advances in alkylations of nitronate anions, alkenes and alkynes, as well as discuss current mechanistic understanding of these novel reactions. PMID:26734076

  2. Palladium-catalyzed Heck-type cross-couplings of unactivated alkyl iodides.

    PubMed

    McMahon, Caitlin M; Alexanian, Erik J

    2014-06-02

    A palladium-catalyzed, intermolecular Heck-type coupling of alkyl iodides and alkenes is described. This process is successful with a variety of primary and secondary unactivated alkyl iodides as reaction partners, including those with hydrogen atoms in the β position. The mild catalytic conditions enable intermolecular C-C bond formations with a diverse set of alkyl iodides and alkenes, including substrates containing base- or nucleophile-sensitive functionality.

  3. Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones.

    PubMed

    Tong, Guanghu; Zhu, Bo; Lee, Richmond; Yang, Wenguo; Tan, Davin; Yang, Caiyun; Han, Zhiqiang; Yan, Lin; Huang, Kuo-Wei; Jiang, Zhiyong

    2013-05-17

    The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared.

  4. Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids.

    PubMed

    Fu, Ming-Chen; Shang, Rui; Cheng, Wan-Min; Fu, Yao

    2015-07-27

    A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts.

  5. Differences in sequence selectivity of DNA alkylation by isomeric intercalating aniline mustards.

    PubMed

    Prakash, A S; Denny, W A; Wakelin, L P

    1990-01-01

    Two DNA-targeted mustard derivatives, N,N-bis(2-chloroethyl)-4-(5-[9-acridinylamino]-pentamido)aniline and 4-(9-[acridinylamino]butyl 4-(N,N-bis[2-chloroethyl]-aminobenzamide, which are isomeric compounds where the mustard is linked to the DNA-binding 9-aminoacridine moiety by either a -CONH- or a -NHCO- group, show significant differences in the sequence selectivity of their alkylation of DNA. The CONH isomer is a more efficient alxylating agent than the NHCO compound by an order of magnitude, consistent with the larger electron release of the CONH group to the aniline ring. However, the pattern of alkylation by the two compounds is also very different, with the CONH isomer preferring alkylation of guanines adjacent to 3'- or 5'-adenines and cytosines (for example those in sequences 5'-CGC, 5'-AGC, 5'-CGG and 5'-AGA) while the isomeric NHCO compound shows preference for guanines in runs of Gs. In addition, both isomers alkylate 3'-adenines in runs of adenines. Both compounds also show completely different patterns of alkylation to their untargeted mustard counterparts, since 4-MeCONH-aniline mustard alkylates all guanines and adenines in runs of adenines, while 4-Me2NCO-aniline mustard fails to alkylate DNA at all. These differences in alkylation patterns between the CONH- and its isomeric NHCO- compounds and their relationships between the alkylation patterns of the isomers and their biological activities are discussed.

  6. Complementary addressed modification and cleavage of a single stranded DNA fragment with alkylating oligonucleotide derivatives.

    PubMed Central

    Vlassov, V V; Zarytova, V F; Kutiavin, I V; Mamaev, S V; Podyminogin, M A

    1986-01-01

    A single stranded DNA fragment was modified with alkylating derivatives of oligonucleotides complementary to a certain nucleotide sequences in the fragment. The derivatives carried aromatic 2-chloroethylamino groups at their 3'- or 5'-terminal nucleotide residues. Some of the derivatives carried both alkylating group and intercalating phenazine group which stabilized complementary complexes. It was found that these oligonucleotide derivatives modify the DNA fragment in a specific way near the target complementary nucleotide sequences, and the DNA fragment can be cleaved at the alkylated nucleotides positions. Alkylating derivatives carrying phenazine groups were found to be the most efficient in reaction with the DNA fragment. Images PMID:3714471

  7. Catalytic Selenium-Promoted Intermolecular Friedel-Crafts Alkylation with Simple Alkenes.

    PubMed

    Tang, E; Zhao, Yinjiao; Li, Wen; Wang, Weilin; Zhang, Meng; Dai, Xin

    2016-03-04

    A method for conducting selenium-promoted intermolecular Friedel-Crafts (F-C) alkylation reactions has been developed with simple alkenes using trimethylsilyl trifluoromethanesulfonate as a catalyst and N-phenylselenophthalimide as an efficient selenium source. Electron-rich arenes smoothly underwent F-C alkylation with a variety of alkenes to afford alkylated products in good yield and with high regioselectivity and diastereoselectivity. The regioselectivity and stereoselectivity of arenes and alkenes as well as a preliminary mechanism of the F-C alkylation reaction are discussed.

  8. Methods of producing alkylated hydrocarbons from an in situ heat treatment process liquid

    DOEpatents

    Roes, Augustinus Wilhelmus Maria; Mo, Weijian; Muylle, Michel Serge Marie; Mandema, Remco Hugo; Nair, Vijay

    2009-09-01

    A method for producing alkylated hydrocarbons is disclosed. Formation fluid is produced from a subsurface in situ heat treatment process. The formation fluid is separated to produce a liquid stream and a first gas stream. The first gas stream includes olefins. The liquid stream is fractionated to produce at least a second gas stream including hydrocarbons having a carbon number of at least 3. The first gas stream and the second gas stream are introduced into an alkylation unit to produce alkylated hydrocarbons. At least a portion of the olefins in the first gas stream enhance alkylation.

  9. Photoinduced, Copper-Catalyzed Carbon-Carbon Bond Formation with Alkyl Electrophiles: Cyanation of Unactivated Secondary Alkyl Chlorides at Room Temperature.

    PubMed

    Ratani, Tanvi S; Bachman, Shoshana; Fu, Gregory C; Peters, Jonas C

    2015-11-04

    We have recently reported that, in the presence of light and a copper catalyst, nitrogen nucleophiles such as carbazoles and primary amides undergo C-N coupling with alkyl halides under mild conditions. In the present study, we establish that photoinduced, copper-catalyzed alkylation can also be applied to C-C bond formation, specifically, that the cyanation of unactivated secondary alkyl chlorides can be achieved at room temperature to afford nitriles, an important class of target molecules. Thus, in the presence of an inexpensive copper catalyst (CuI; no ligand coadditive) and a readily available light source (UVC compact fluorescent light bulb), a wide array of alkyl halides undergo cyanation in good yield. Our initial mechanistic studies are consistent with the hypothesis that an excited state of [Cu(CN)2](-) may play a role, via single electron transfer, in this process. This investigation provides a rare example of a transition metal-catalyzed cyanation of an alkyl halide, as well as the first illustrations of photoinduced, copper-catalyzed alkylation with either a carbon nucleophile or a secondary alkyl chloride.

  10. Photoinduced, Copper-Catalyzed Carbon–Carbon Bond Formation with Alkyl Electrophiles: Cyanation of Unactivated Secondary Alkyl Chlorides at Room Temperature

    PubMed Central

    Ratani, Tanvi S.; Bachman, Shoshana; Fu, Gregory C.; Peters, Jonas C.

    2015-01-01

    We have recently reported that, in the presence of light and a copper catalyst, nitrogen nucleophiles such as carbazoles and primary amides undergo C–N coupling with alkyl halides under mild conditions. In the present study, we establish that photoinduced, copper-catalyzed alkylation can also be applied to C–C bond formation, specifically, that the cyanation of unactivated secondary alkyl chlorides can be achieved at room temperature to afford nitriles, an important class of target molecules. Thus, in the presence of an inexpensive copper catalyst (CuI; no ligand co-additive) and a readily available light source (UVC compact fluorescent light bulb), a wide array of alkyl halides undergo cyanation in good yield. Our initial mechanistic studies are consistent with the hypothesis that an excited state of [Cu(CN)2]− may play a role, via single electron transfer, in this process. This investigation provides a rare example of a transition metal-catalyzed cyanation of an alkyl halide, as well as the first illustrations of photoinduced, copper-catalyzed alkylation with either a carbon nucleophile or a secondary alkyl chloride. PMID:26491957

  11. Synthesis and luminescence properties of 2-(benzylcarbamoyl)phenyl derivatives and their europium complexes.

    PubMed

    Guo, Dongcai; He, Wei; Liu, Bang; Gou, Lining; Li, Ruixia

    2013-01-01

    Six novel 2-(benzylcarbamoyl)phenyl derivatives were synthesized and characterized by (1) H-NMR, mass spectrometry, infrared spectra and elemental analysis. Their europium complexes were prepared and characterized by elemental analysis, EDTA titrimetric analysis, IR and UV spectra as well as molar conductivity measurements. The luminescence properties of these complexes were investigated and results show that 2-(benzylcarbamoyl)phenyl derivatives possess high selectivity and good coordination with the europium ion. Complex Eu-2-(benzylcarbamoyl)phenyl-2-phenylacetate showed green luminescence that was emitted by the ligand of 2-(benzylcarbamoyl)phenyl-2-phenylacetate, while other complexes showed the characteristic red luminescence of europium ion and also possessed high luminescence intensity.

  12. Phenyl Acetate Preparation from Phenol and Acetic Acid: Reassessment of a Common Textbook Misconception.

    ERIC Educational Resources Information Center

    Hocking, M. B.

    1980-01-01

    Reassesses a common textbook misconception that "...phenols cannot be esterified directly." Results of experiments are discussed and data tables provided of an effective method for the direct preparation of phenyl acetate. (CS)

  13. Tetratopic phenyl compounds, related metal-organic framework materials and post-assembly elaboration

    DOEpatents

    Farha, Omar K.; Hupp, Joseph T.

    2012-09-11

    Disclosed are tetratopic carboxylic acid phenyl for use in metal-organic framework compounds. These compounds are useful in catalysis, gas storage, sensing, biological imaging, drug delivery and gas adsorption separation.

  14. Tetratopic phenyl compounds, related metal-organic framework materials and post-assembly elaboration

    DOEpatents

    Farha, Omar K; Hupp, Joseph T

    2013-06-25

    Disclosed are tetratopic carboxylic acid phenyl for use in metal-organic framework compounds. These compounds are useful in catalysis, gas storage, sensing, biological imaging, drug delivery and gas adsorption separation.

  15. Effects of Structure and Environment on the Spectroscopic Properties of (3-Amino-Substituted-Thieno[2,3-b] Pyridine-2-yl)Pyridine/Quinolin-2-yl)(Phenyl)Methanones: Experimental and Theoretical Study.

    PubMed

    Al-Ansari, Ibrahim Ahmed Z

    2016-05-01

    The electronic absorption, excitation and fluorescence properties of two 3-amino-substituted-thieno[2,3-b]pyridine/quinolin-2-yl)(phenyl)methanones; (referred to as compounds 1-2: where 3-amino-4,5,6-trimethyl-thieno[2,3-b]pyridin-2-yl)(phenyl)methanone (1); and 3-amino-5,6,7,8-tetrahydro-thieno[2,3-b]quinolin-2-yl)(phenyl)methanone (2)) have been investigated in solvents of various polarity and hydrogen-bonding abilities. Results based on the electronic absorption, excitation and emission study of these compounds; indicated that singlets (S1 and S2) excited-states are populated in non-polar and polar protic/aprotic solvents giving dual fluorescence with weak charge transfer separation. The experimental results were interpreted with the aid of quantum chemistry calculations carried out with the DFT and TD-DFT/B3lyp/6-31 + G(d,p) methods. Based on these calculations, compounds 1-2 exist in two rotamers: anti and syn, separated by ca. 5-6 kcal mol(-1) energy barriers in favor of the anti-conformer. The anti-structure, was shown to be stabilized through existence of intramolecular NH…O hydrogen bond (H-b), which plays a dominant role in affecting the energy of the HOMO-1 molecular orbital. Further, methyl/alkyl substitution in the pyridyl-thiophene ring was shown to involve in σ-π hyper-conjugation and destabilization of the HOMO-1 MO's.

  16. Photoluminescence of 1-phenyl,3-methyl pyrazoloquinoline derivatives

    NASA Astrophysics Data System (ADS)

    Koścień, E.; Gondek, E.; Jarosz, B.; Danel, A.; Nizioł, J.; Kityk, A. V.

    2009-04-01

    Paper presents the absorption and photoluminescence of 7-TFM, 6-F, 6-CN, 6-TBu and 6-COOEt derivatives of 1-phenyl-3-methyl-1 H-Pyrazolo[3,4- b]quinoline (MPPQ). The measured spectra are compared with the results of the quantum chemical calculations performed by means of the semi-empirical methods (AM1 or PM3) that have been applied either to the equilibrium molecular conformations in vacuo ( T=0 K) or combined with the MD simulations ( T=300 K). The photoluminescent spectra of MPPQ dyes are highly solvatochromic. The emission bands broaden and shift to the red with the increasing of solvent polarity, indicating thus a substantial dipole moment of the excited states. According to the quantum chemical analysis the reason for the strong solvatochromism of MPPQ dyes is related with intramolecular charge transfer (ICT) state. Due to the large dipole moment in the twisted geometry the ICT state is believed to become the lowest excited state in a strongly polar environment. This would explain a considerable solvatochromic shift in the highly polar solvents observed for all MPPQ dyes in the experiment. Such hypothesis is supported by the semi-empirical quantum chemical evaluations.

  17. 1-Phenyl-4-(triphenyl­phosphanyl­idene)pyrrolidine-2,3,5-trione

    PubMed Central

    Fan, Da-He

    2008-01-01

    In the title compound, C28H20NO3P, the five-membered maleimide ring is almost planar. The inter­planar angles between the maleimide ring and the three P-bound phenyl rings are 70.6 (2), 60.4 (2) and 54.68 (18)°, while the dihedral angle between the maleimide ring and the N-bound phenyl group is 55.43 (19)°. PMID:21201913

  18. Catalytic Intramolecular Ketone Alkylation with Olefins by Dual Activation.

    PubMed

    Lim, Hee Nam; Dong, Guangbin

    2015-12-07

    Two complementary methods for catalytic intramolecular ketone alkylation reactions with unactivated olefins, resulting in Conia-ene-type reactions, are reported. The transformations are enabled by dual activation of both the ketone and the olefin and are atom-economical as stoichiometric oxidants or reductants are not required. Assisted by Kool's aniline catalyst, the reaction conditions can be both pH- and redox-neutral. A broad range of functional groups are thus tolerated. Whereas the rhodium catalysts are effective for the formation of five-membered rings, a ruthenium-based system that affords the six-membered ring products was also developed.

  19. Tunneling conductance of amine-linked alkyl chains.

    PubMed

    Prodan, Emil; Car, Roberto

    2008-06-01

    The tunneling transport theory developed in ref 9 (Phys. Rev. B 2007, 76, 115102) is applied to molecular devices made of alkyl chains linked to gold electrodes via amine groups. Using the analytic expression of the tunneling conductance derived in our previous work, we identify the key physical quantities that characterize the conductance of these devices. By investigating the transport characteristics of three devices, containing four, six, and eight methyl groups, we extract the dependence of the tunneling conductance on the chain's length, which is an exponential decay law in agreement with recent experimental data.

  20. Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones.

    PubMed

    Craig, Robert A; Loskot, Steven A; Mohr, Justin T; Behenna, Douglas C; Harned, Andrew M; Stoltz, Brian M

    2015-11-06

    The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)3-t-BuPHOX ligand, α-quaternary cyclopentanones were isolated in yields up to >99% with ee's up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.

  1. Carcinogenic potency of alkylating agents in rodents and humans.

    PubMed

    Dedrick, R L; Morrison, P F

    1992-05-01

    Alkylating agents are known to produce second tumors in cancer patients treated for their primary cancer. Since therapeutic doses are high and the pharmacokinetics of the drugs are thoroughly studied, these agents provide a unique opportunity to compare intrinsic carcinogenic potency between experimental animals and humans. We have examined the carcinogenicity of melphalan, chlorambucil, and cyclophosphamide in causing leukemia in patients treated for cancer or polycythemia vera and lymphosarcoma in rats and mice. A good correlation among species is observed when the carcinogenic potency is based on the total lifetime exposure to active species derived from these drugs.

  2. Synthesis and biological studies of N-alkylated cyclic diamines.

    PubMed

    Xiong, Xiao-Qin; Liang, Feng; Yang, Li; Zhou, Xiang; Zheng, Cong-Yi; Cao, Xiao-Ping

    2007-01-01

    Several alkyl-substituted mesocyclic diamines were synthesized, and their interaction with DNA were studied by melting-temperature measurements and the ethidium bromide (EB)-fluorescence competitive method. The supercoiled DNA hydrolytic cleavage by 1,4-dioctyl-1,4-diazepan-6-ol (4) was supported by the evidence from free-radical quenching and T4-ligase ligation. Preliminary pharmacological tests showed that only 1,4-dioctyl-1,4-diazepan-6-ol (4) had antitumor activity against HeLa cell lines in vitro.

  3. Synthesis of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}-N-substituted acetamides as potential antimicrobial and hemolytic agents.

    PubMed

    Rehman, Aziz-ur; Abbasi, Muhammad Athar; Siddiqui, Sabahat Zahra; Ahmad, Irshad; Shahid, Muhammad; Subhani, Zinayyera

    2016-05-01

    A new series of N-substituted derivatives of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}acetamides was synthesized. The synthesis was carried out by converting benzoic acid (1) into ethyl benzoate (2), benzohydrazide (3) and then 5-pheny-1,3,4-Oxadiazol-2-thiol (4) step by st0ep. The target compounds 6a-p were synthesized by reaction of compound 4 with equimolar ratios of different N-alkyl/aryl substituted 2-bromoacetamide (5a-p) in the presence of DMF and sodium hydride (NaH). The spectral (EI-MS, IR, (1)H-NMR) characterization of all the synthesized compounds reveal their successful synthesis. The compounds were also screened for antimicrobial & hemolytic activity and most of them were found to be active against the selected microbial species at variable extent relative to reference standards. But 6h was the most active against the selected panel of microbes. This series showed less toxicity and may be considered for further biological screening and application trial except 6m, possessing higher cytotoxicity.

  4. A General Alkyl-Alkyl Cross-Coupling Enabled by Redox-Active Esters and Alkylzinc Reagents

    PubMed Central

    Qin, Tian; Cornella, Josep; Li, Chao; Malins, Lara R.; Edwards, Jacob T.; Kawamura, Shuhei; Maxwell, Brad D.; Eastgate, Martin D.; Baran, Phil S.

    2016-01-01

    Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to make simple C–N (amide) bonds from carboxylic acids with loss of water can be employed to make C–C bonds through coupling with dialkylzinc reagents and loss of carbon dioxide. This disconnection strategy benefits from the use of a simple, inexpensive nickel catalyst and exhibits a remarkably broad scope across a range of substrates (>70 examples). PMID:27103669

  5. Antibacterial Activity of Alkyl Gallates against Xanthomonas citri subsp. citri

    PubMed Central

    Silva, I. C.; Regasini, L. O.; Petrônio, M. S.; Silva, D. H. S.; Bolzani, V. S.; Belasque, J.; Sacramento, L. V. S.

    2013-01-01

    The plant-pathogenic bacterium Xanthomonas citri subsp. citri is the causal agent of Asiatic citrus canker, a serious disease that affects all the cultivars of citrus in subtropical citrus-producing areas worldwide. There is no curative treatment for citrus canker; thus, the eradication of infected plants constitutes the only effective control of the spread of X. citri subsp. citri. Since the eradication program in the state of São Paulo, Brazil, is under threat, there is a clear risk of X. citri subsp. citri becoming endemic in the main orange-producing area in the world. Here we evaluated the potential use of alkyl gallates to prevent X. citri subsp. citri growth. These esters displayed a potent anti-X. citri subsp. citri activity similar to that of kanamycin (positive control), as evaluated by the resazurin microtiter assay (REMA). The treatment of X. citri subsp. citri cells with these compounds induced altered cell morphology, and investigations of the possible intracellular targets using X. citri subsp. citri strains labeled for the septum and centromere pointed to a common target involved in chromosome segregation and cell division. Finally, the artificial inoculation of citrus with X. citri subsp. citri cells pretreated with alkyl gallates showed that the bacterium loses the ability to colonize its host, which indicates the potential of these esters to protect citrus plants against X. citri subsp. citri infection. PMID:23104804

  6. The isobutylene-isobutane alkylation process in liquid HF revisited.

    PubMed

    Esteves, P M; Araújo, C L; Horta, B A C; Alvarez, L J; Zicovich-Wilson, C M; Ramírez-Solís, A

    2005-07-07

    Details on the mechanism of HF catalyzed isobutylene-isobutane alkylation were investigated. On the basis of available experimental data and high-level quantum chemical calculations, a detailed reaction mechanism is proposed taking into account solvation effects of the medium. On the basis of our computational results, we explain why the density of the liquid media and stirring rates are the most important parameters to achieve maximum yield of alkylate, in agreement with experimental findings. The ab initio Car-Parrinello molecular dynamics calculations show that isobutylene is irreversibly protonated in the liquid HF medium at higher densities, leading to the ion pair formation, which is shown to be a minimum on the potential energy surface after optimization using periodic boundary conditions. The HF medium solvates preferentially the fluoride anion, which is found as solvated [FHF](-) or solvated F(-.)(HF)(3). On the other hand, the tert-butyl cation is weakly solvated, where the closest HF molecules appear at a distance of about 2.9 Angstrom with the fluorine termination of an HF chain.

  7. Bioaccumulation of perfluorinated alkyl acids: observations and models.

    PubMed

    Ng, Carla A; Hungerbühler, Konrad

    2014-05-06

    In this review, we consider the two prevailing hypotheses for the mechanisms that control the bioaccumulation of perfluorinated alkyl acids (PFAAs). The first assumes that partitioning to membrane phospholipids, which have a higher affinity for charged species than neutral storage lipids, can explain the high bioaccumulation potential of these compounds. The second assumes that interactions with proteins--including serum albumin, liver fatty acid binding proteins (L-FABP), and organic anion transporters--determine the distribution, accumulation and half-lives of PFAAs. We consider three unique phenomena to evaluate the two models: (1) observed patterns of tissue distribution in the laboratory and field, (2) the relationship between perfluorinated chain length and bioaccumulation, and (3) species- and gender-specific variation in elimination half-lives. Through investigation of these three characteristics of PFAA bioaccumulation, we show the strengths and weaknesses of the two modeling approaches. We conclude that the models need not be mutually exclusive, but that protein interactions are needed to explain some important features of PFAA bioaccumulation. Although open questions remain, further research should include perfluorinated alkyl substances (PFASs) beyond the long-chain PFAAs, as these substances are being phased out and replaced by a wide variety of PFASs with largely unknown properties and bioaccumulation behavior.

  8. Differential alkylation-based redox proteomics--Lessons learnt.

    PubMed

    Wojdyla, Katarzyna; Rogowska-Wrzesinska, Adelina

    2015-12-01

    Cysteine is one of the most reactive amino acids. This is due to the electronegativity of sulphur atom in the side chain of thiolate group. It results in cysteine being present in several distinct redox forms inside the cell. Amongst these, reversible oxidations, S-nitrosylation and S-sulfenylation are crucial mediators of intracellular redox signalling, with known associations to health and disease. Study of their functionalities has intensified thanks to the development of various analytical strategies, with particular contribution from differential alkylation-based proteomics methods. Presented here is a critical evaluation of differential alkylation-based strategies for the analysis of S-nitrosylation and S-sulfenylation. The aim is to assess the current status and to provide insights for future directions in the dynamically evolving field of redox proteomics. To achieve that we collected 35 original research articles published since 2010 and analysed them considering the following parameters, (i) resolution of modification site, (ii) quantitative information, including correction of modification levels by protein abundance changes and determination of modification site occupancy, (iii) throughput, including the amount of starting material required for analysis. The results of this meta-analysis are the core of this review, complemented by issues related to biological models and sample preparation in redox proteomics, including conditions for free thiol blocking and labelling of target cysteine oxoforms.

  9. The effect of alkylating agents on male rat fertility

    PubMed Central

    Jackson, H.; Fox, B. W.; Craig, A. W.

    1959-01-01

    The effects of tumour inhibitory doses of tretamine (triethylenemelamine), busulphan, and melphalan on the fertility of male rats have been examined. The aromatic nitrogen mustard, melphalan, was inactive, but busulphan has a highly selective action on spermatogenesis which contrasts strikingly with that of tretamine. The main action of tretamine was exerted upon spermatocytes or spermatids, but, with increasing dose, the effects spread to involve a wide range of spermatogenic cells including mature sperm, so that infertility could be induced very rapidly. Busulphan, however, interfered with the development of spermatogonia for several weeks, although other germinal cells were unaffected and continued to develop into mature spermatozoa. This accounted for the continuation of normal fertility for 7 weeks after a dose, before sterility suddenly developed. The antifertility activity of tretamine could be simulated by a variety of other ethyleneimino compounds, potency being greatest in trifunctional and least in monofunctional compounds. The latter were, however, very destructive to the seminiferous epithelium with increasing dose. In the rat, there appeared to be no definite relationship between the ability of alkylating substances to interfere with the activity of normal and pathological proliferating tissues, as represented by the germinal epithelium, haematopoietic, and tumour tissue. Although carcinogenicity was a biological property of alkylating agents, other chemical types of carcinogen did not interfere with fertility. ImagesFIG. 2aFIG. 2bFIG. 2c PMID:13662565

  10. N-Alkyl-Substituted Isatins Enhance P2X7 Receptor-Induced Interleukin-1β Release from Murine Macrophages.

    PubMed

    Sluyter, Ronald; Vine, Kara L

    2016-01-01

    Extracellular adenosine 5'-triphosphate (ATP) activates the P2X7 receptor channel to induce the rapid release of the proinflammatory cytokine, interleukin- (IL-) 1β, from macrophages. Microtubule rearrangements are thought to be involved in this process. Some isatin derivatives alter microtubules and display anticancer activities. The current study investigated the effect of isatin and seven structurally diverse isatin derivatives on P2X7-mediated IL-1β release from murine J774 macrophages. ATP-induced IL-1β and lactate dehydrogenase (LDH) release were assessed by specific colorimetric assays. P2X7 activity was determined by flow cytometric measurements of ATP-induced cation dye uptake. Cytotoxicity of isatin derivatives was determined using a tetrazolium-based colorimetric assay. ATP caused rapid IL-1β release in a concentration-dependent manner, and this process was completely impaired by the P2X7 antagonist, AZ10606120. In contrast, 5,7-dibromo-N-(p-methoxybenzyl)isatin (NAI) and 3-{4-[5,7-dibromo-1-(4-methoxybenzyl)-2-oxoindolin-3-ylidenamino]phenyl}propanoic acid (NAI-imine) enhanced P2X7-induced IL-1β release by twofold compared to that of isatin and the parent molecule, 5,7-dibromoisatin. NAI and NAI-imine had minimal effect on P2X7-induced dye uptake and LDH release. In contrast, 24-hour incubation with NAI and NAI-imine (in the absence of exogenous ATP) induced macrophage death in a concentration-dependent manner. In conclusion, this study demonstrates that N-alkyl-substituted isatins enhance P2X7 receptor-induced IL-1β release from murine macrophages. Thus, in addition to direct anticancer effects, these compounds may also impact inflammatory and immune cells within the tumor microenvironment.

  11. Heterogeneous catalysis by solid superacids--14. Perfluorinated resinsulfonic acid (nafion-h) catalyzed Friedel-crafts alkylation of toluene and phenol with alkyl chloroformates and oxalates

    SciTech Connect

    Olah, G.A.; Meidar, D.; Malhotra, R.; Olah, J.A.; Narang, S.C.

    1980-01-01

    Product distributions obtained in the alkylation of toluene with methyl, ethyl, and isopropyl chloroformate and dimethyl oxalate and of phenol with methyl and ethyl chloroformate and dimethyl- and diethyloxalate.

  12. 40 CFR 721.520 - Alanine, N-(2-carboxyethyl)-N-alkyl-, salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-, salt. 721.520 Section 721.520 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.520 Alanine, N-(2-carboxyethyl)-N-alkyl-, salt. (a) Chemical substance... alanine, N-(2-carboxyethyl)-N- alkyl-, salt (P-89-336) is subject to reporting under this section for...

  13. 40 CFR 721.520 - Alanine, N-(2-carboxyethyl)-N-alkyl-, salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-, salt. 721.520 Section 721.520 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.520 Alanine, N-(2-carboxyethyl)-N-alkyl-, salt. (a) Chemical substance... alanine, N-(2-carboxyethyl)-N- alkyl-, salt (P-89-336) is subject to reporting under this section for...

  14. A new procedure for N1-alkylation of imidazolidin-4-ones and its NMR characterization

    NASA Astrophysics Data System (ADS)

    Vale, Nuno; Figueiredo, Patrícia

    2016-12-01

    N1-unsubstituted imidazolidin-4-ones of primaquine (PQ) can be stabilized by N1-alkylation under basic conditions. Here we report the development, with our conditions, of peptidomimetic derivatives of PQ with L-amino acid and alkyl derivatives. The new derivatives represent potential new therapeutics for use against protozoan parasites, through enzymatic protection of aminopeptidases.

  15. 40 CFR 721.10361 - Anthraquinonedicarboximide, diamino-N-alkyl- (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Anthraquinonedicarboximide, diamino-N... Specific Chemical Substances § 721.10361 Anthraquinonedicarboximide, diamino-N-alkyl- (generic). (a... generically as anthraquinonedicarboximide, diamino-N-alkyl- (PMN P-10-15) is subject to reporting under...

  16. 40 CFR 721.10361 - Anthraquinonedicarboximide, diamino-N-alkyl- (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Anthraquinonedicarboximide, diamino-N... Specific Chemical Substances § 721.10361 Anthraquinonedicarboximide, diamino-N-alkyl- (generic). (a... generically as anthraquinonedicarboximide, diamino-N-alkyl- (PMN P-10-15) is subject to reporting under...

  17. 40 CFR 721.10361 - Anthraquinonedicarboximide, diamino-N-alkyl- (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Anthraquinonedicarboximide, diamino-N... Specific Chemical Substances § 721.10361 Anthraquinonedicarboximide, diamino-N-alkyl- (generic). (a... generically as anthraquinonedicarboximide, diamino-N-alkyl- (PMN P-10-15) is subject to reporting under...

  18. Synthesis and antifungal activity of natural product-based 6-alkyl-2 3 4 5-tetrahydropyridines

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Seven 6-alkyl-2,3,4,5-tetrahydropyridines (5a–5g) that mimic the natural products piperideines that were recently identified in the fire ant venom have been synthesized. Compounds 5c–5g with the C-6 alkyl chain lengths from C14 to C18 showed varying degrees of antifungal activities, with 5e (6-hexa...

  19. 40 CFR 721.10417 - Biphenyl alkyl morpholino ketone (generic) (P-11-338).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... (generic) (P-11-338). 721.10417 Section 721.10417 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10417 Biphenyl alkyl morpholino ketone (generic) (P-11-338). (a... generically as biphenyl alkyl morpholino ketone (PMN P-11-338) is subject to reporting under this section...

  20. 40 CFR 721.10417 - Biphenyl alkyl morpholino ketone (generic) (P-11-338).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... (generic) (P-11-338). 721.10417 Section 721.10417 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10417 Biphenyl alkyl morpholino ketone (generic) (P-11-338). (a... generically as biphenyl alkyl morpholino ketone (PMN P-11-338) is subject to reporting under this section...

  1. 40 CFR 721.10417 - Biphenyl alkyl morpholino ketone (generic) (P-11-338).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... (generic) (P-11-338). 721.10417 Section 721.10417 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.10417 Biphenyl alkyl morpholino ketone (generic) (P-11-338). (a... generically as biphenyl alkyl morpholino ketone (PMN P-11-338) is subject to reporting under this section...

  2. Palladium-Catalyzed Heteroarylation and Concomitant ortho-Alkylation of Aryl Iodides.

    PubMed

    Lei, Chuanhu; Jin, Xiaojia; Zhou, Jianrong Steve

    2015-11-02

    Three-component couplings were achieved from common aryl halides, alkyl halides, and heteroarenes under palladium and norbornene co-catalysis. The reaction forges hindered aryl-heteroaryl bonds and introduces ortho-alkyl groups to aryl rings. Various heterocycles such as oxazoles, thiazoles and thiophenes underwent efficient coupling. The heteroarenes were deprotonated in situ by bases without the assistance of palladium catalysts.

  3. 40 CFR 721.10621 - Distillation bottoms, alkylated benzene by-product (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... benzene by-product (generic). 721.10621 Section 721.10621 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10621 Distillation bottoms, alkylated benzene by... substance identified generically as distillation bottoms, alkylated benzene by-product (PMN P-12-196)...

  4. 40 CFR 721.10621 - Distillation bottoms, alkylated benzene by-product (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... benzene by-product (generic). 721.10621 Section 721.10621 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10621 Distillation bottoms, alkylated benzene by... substance identified generically as distillation bottoms, alkylated benzene by-product (PMN P-12-196)...

  5. 40 CFR 721.5860 - Methylphenol, bis(sub-sti-tuted)alkyl.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Methylphenol, bis(sub-sti-tuted)alkyl... Substances § 721.5860 Methylphenol, bis(sub-sti-tuted)alkyl. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as methylphenol,...

  6. Alkyl-π engineering in state control toward versatile optoelectronic soft materials

    PubMed Central

    Lu, Fengniu; Nakanishi, Takashi

    2015-01-01

    Organic π-conjugated molecules with extremely rich and tailorable electronic and optical properties are frequently utilized for the fabrication of optoelectronic devices. To achieve high solubility for facile solution processing and desirable softness for flexible device fabrication, the rigid π units were in most cases attached by alkyl chains through chemical modification. Considerable numbers of alkylated-π molecular systems with versatile applications have been reported. However, a profound understanding of the molecular state control through proper alkyl chain substitution is still highly demanded because effective applications of these molecules are closely related to their physical states. To explore the underlying rule, we review a large number of alkylated-π molecules with emphasis on the interplay of van der Waals interactions (vdW) of the alkyl chains and π–π interactions of the π moieties. Based on our comprehensive investigations of the two interactions’ impacts on the physical states of the molecules, a clear guidance for state control by alkyl-π engineering is proposed. Specifically, either with proper alkyl chain substitution or favorable additives, the vdW and π–π interactions can be adjusted, resulting in modulation of the physical states and optoelectronic properties of the molecules. We believe the strategy summarized here will significantly benefit the alkyl-π chemistry toward wide-spread applications in optoelectronic devices. PMID:27877748

  7. 76 FR 6335 - Sodium and Potassium Salts of N-alkyl (C8

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-02-04

    ... AGENCY 40 CFR Part 180 Sodium and Potassium Salts of N-alkyl (C 8 - C 18 )-beta-iminodipropionic acid... residues of sodium and potassium salts of N-alkyl (C 8 -C 18 )-beta-iminodipropionic acid where the C 8 -C.... EPA previously published a final rule to establish a tolerance exemption for sodium salts of SSNA...

  8. 40 CFR 721.10497 - Substituted alkyl ester, hydrolysis products with silica and substituted silane (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted alkyl ester, hydrolysis... ester, hydrolysis products with silica and substituted silane (generic). (a) Chemical substance and... alkyl ester, hydrolysis products with silica and substituted silane (PMNs P-06-276 and P-06-279)...

  9. 40 CFR 721.10497 - Substituted alkyl ester, hydrolysis products with silica and substituted silane (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted alkyl ester, hydrolysis... ester, hydrolysis products with silica and substituted silane (generic). (a) Chemical substance and... alkyl ester, hydrolysis products with silica and substituted silane (PMNs P-06-276 and P-06-279)...

  10. 40 CFR 721.10350 - Amines, C11-14-branched and linear alkyl.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Amines, C11-14-branched and linear... Specific Chemical Substances § 721.10350 Amines, C11-14-branched and linear alkyl. (a) Chemical substance...-branched and linear alkyl (PMN P-06-742; CAS No. 863766-30-7) is subject to reporting under this...

  11. 40 CFR 721.10350 - Amines, C11-14-branched and linear alkyl.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Amines, C11-14-branched and linear... Specific Chemical Substances § 721.10350 Amines, C11-14-branched and linear alkyl. (a) Chemical substance...-branched and linear alkyl (PMN P-06-742; CAS No. 863766-30-7) is subject to reporting under this...

  12. 40 CFR 721.10350 - Amines, C11-14-branched and linear alkyl.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Amines, C11-14-branched and linear... Specific Chemical Substances § 721.10350 Amines, C11-14-branched and linear alkyl. (a) Chemical substance...-branched and linear alkyl (PMN P-06-742; CAS No. 863766-30-7) is subject to reporting under this...

  13. 40 CFR 721.950 - Sodium salt of an alkylated, sulfonated aromatic (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., sulfonated aromatic (generic name). 721.950 Section 721.950 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.950 Sodium salt of an alkylated, sulfonated... chemical substance identified generically as a sodium salt of an alkylated, sulfonated aromatic (PMN...

  14. 40 CFR 721.950 - Sodium salt of an alkylated, sulfonated aromatic (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., sulfonated aromatic (generic name). 721.950 Section 721.950 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.950 Sodium salt of an alkylated, sulfonated... chemical substance identified generically as a sodium salt of an alkylated, sulfonated aromatic (PMN...

  15. REVISITING CLASSICAL NUCLEOPHILIC SUBSTITUTIONS IN AQUEOUS MEDIUM: MICROWAVE-ASSISTED SYNTHESIS OF ALKYL AZIDES

    EPA Science Inventory

    An efficient and clean synthesis of alkyl azides using microwave (MW) radiation is described in aqueous medium by reacting alkyl halides or tosylates with alkali azides. This general and expeditious MW-enhanced approach to nucleophilic substitution reactions is applicable to the ...

  16. 40 CFR 721.520 - Alanine, N-(2-carboxyethyl)-N-alkyl-, salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-, salt. 721.520 Section 721.520 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.520 Alanine, N-(2-carboxyethyl)-N-alkyl-, salt. (a) Chemical substance... alanine, N-(2-carboxyethyl)-N- alkyl-, salt (P-89-336) is subject to reporting under this section for...

  17. 40 CFR 721.520 - Alanine, N-(2-carboxyethyl)-N-alkyl-, salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-, salt. 721.520 Section 721.520 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.520 Alanine, N-(2-carboxyethyl)-N-alkyl-, salt. (a) Chemical substance... alanine, N-(2-carboxyethyl)-N- alkyl-, salt (P-89-336) is subject to reporting under this section for...

  18. 40 CFR 721.520 - Alanine, N-(2-carboxyethyl)-N-alkyl-, salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-, salt. 721.520 Section 721.520 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.520 Alanine, N-(2-carboxyethyl)-N-alkyl-, salt. (a) Chemical substance... alanine, N-(2-carboxyethyl)-N- alkyl-, salt (P-89-336) is subject to reporting under this section for...

  19. Versatile assembly of p-carboxylatocalix[4]arene-O-alkyl ethers

    SciTech Connect

    Kennedy, Stuart; Teat, Simon J.; Dalgarno, Scott J.

    2009-07-08

    Crystallisation of lower-rim tetra-O-alkylated p-carboxylatocalix[4]arenes from pyridine results in the formation of both bi-layer and pillar type supramolecular motifs. Full alkylation at the calixarene lower rim has significant influence over the supramolecular self-assembly motif, including preclusion of pyridine guest molecules from the calixarene cavity in the solid state.

  20. Formation of furan fatty alkyl esters from their bis-epoxide fatty esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Reactions of epoxidized alkyl soyate with four different alcohols: ethanol, isopropyl alcohol, 2-ethylhexanol, and benzyl alcohol were investigated in the presence of Bronsted acid catalyst. Products not reported in prior studies of similar reactions were found. These were furan fatty acid alkyl est...