Category: 13312-84-0

Noe, Christian R. published the artcileChiral lactols. XIII. On the determination of the absolute configuration of aromatic cyanohydrins and structurally related compounds, Quality Control of 13312-84-0, the publication is Liebigs Annalen (1995), 1353-60, database is CAplus.

Synthesis and conformational anal. of diastereomeric acetals, e.g. I, of aromatic cyanohydrins and structurally related compounds are described. Based on ¹H-NMR spectroscopic and x-ray data it is shown that the absolute configuration of such compounds can be assigned according to a method, which has been presented previously for secondary arylalkyl alcs.

Liebigs Annalen published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Quality Control of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Noe, C. R. published the artcileAmino alcohols. II: Preparation of enantiomerically pure pharmacologically active β-amino alcohols, Computed Properties of 13312-84-0, the publication is Monatshefte fuer Chemie (1995), 126(4), 481-94, database is CAplus.

A synthesis of β-amino alcs. is described starting from racemic or enantiomerically pure α-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminum hydride yielded O-protected β-amino alcs. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected amino alcs. were separated Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure β-amino alcs. or their corresponding hydrochlorides. For example, the chiral synthesis of (R)-1-amino-3-(1-naphthalenyloxy)-2-propanol and (S)-1-amino-3-(1-naphthalenyloxy)-2-propanol was accomplished via resolution of (±)-2-hydroxy-3-(1-naphthalenyloxy)propanenitrile.

Monatshefte fuer Chemie published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Computed Properties of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kodama, Koichi published the artcileCyanative self-condensation of aromatic aldehydes promoted by VO(OⁱPr)₃-Lewis base as a cooperative catalyst, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Organic & Biomolecular Chemistry (2012), 10(47), 9440-9446, database is CAplus and MEDLINE.

In the presence of oxovanadium triisopropoxide and an amine such as 4-dimethylaminopyridine, aromatic aldehydes underwent self-condensation with trimethylsilyl cyanide under an oxygen atm. in acetonitrile to give α-cyanobenzyl benzoates RCH(CN)OCOR (R = Ph, 2-ClC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-MeC₆H₄, 2-MeOC₆H₄, 3-MeOC₆H₄, 4-MeOC₆H₄) (I) in 28-81% conversions and with 93:7-99:1 chemoselectivity for the cyanobenzyl benzoates over the corresponding cyanohydrins. A variety of Lewis base additives acted as cocatalysts for the reaction; reactions performed under nitrogen gave similar conversions but reduced selectivities for cyanobenzyl benzoates. The choice of solvent also altered chemoselectivity significantly. When (R)-PhCHMeNMe₂ was used as a Lewis basic cocatalyst, (S)-I (R = 4-ClC₆H₄) was obtained in 61% conversion, 99:1 chemoselectivity, and 8% ee.

Organic & Biomolecular Chemistry published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Zou, Shuping published the artcileA integrated process for nitrilase-catalyzed asymmetric hydrolysis and easy biocatalyst recycling by introducing biocompatible biphasic system, COA of Formula: C8H6ClNO, the publication is Bioresource Technology (2021), 320(Part_B), 124392, database is CAplus and MEDLINE.

The whole-cell nitrilase-catalyzed asym. hydrolysis of nitriles is a green and efficient preparation approach for chiral carboxylic acids, but often suffers from toxicity and cell lysis from organic substrates. In this work, a novel integrated process for whole-cell nitrilase-catalyzed asym. hydrolysis was developed for the first time by introducing a biocompatible ionic liquid (IL)-based biphasic system. The whole-cell nitrilases displayed an outstanding stability and recyclability in the biphasic system and still retained > 85% activity even after 7 cycles reaction. A preparative-scale fed-batch hydrolysis of o-chloromandelonitrile to (R)-o-chloromandelic acid (R-CMA) was performed using the integrated process. The results revealed a yield of 91.3% and a space-time yield of 746.4 g·L^-1·d^-1, which are currently the highest reported values for R-CMA biosynthesis. The proposed integrated process avoids substrate inhibition, facilitates the reusability of whole-cell nitrilases, and thus shows great potential for the sustainable production of chiral carboxylic acids.

Bioresource Technology published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C6H5F4NO3S, COA of Formula: C8H6ClNO.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Xu, Hong-mei published the artcilePreparation of (R)-o-chloromandelic acid through dynamic kinetic resolution of o-chloromandelonitrile by whole cells of Alcaligenes faecalis CGMCC 1.2006, Quality Control of 13312-84-0, the publication is Fenzi Cuihua (2014), 28(2), 174-181, database is CAplus.

Alcaligenes faecalis CGMCC 1.2006 with higher arylacetonitrilase activity and moderate enantioselectivity towards o-chloromandelonitrile was screened from six microbial strains belonging to Alcaligenes faecalis. The regulating effects of reaction medium on both activity and enantioselectivity of arylacetonitrilase were studied. The addition of water-soluble co-solvents such as methanol into the reaction medium decreased the activity of arylacetonitrilase, but enhanced the enantioselectivity significantly. Addition of non-ionic surfactants possessed the reverse effects. The effects of reaction conditions such as substrate concentration, cell concentration, pH, temperature and reaction time on the activity and enantioselectivity of arylacetonitrilase were also optimized systematically. Under the optimal reaction conditions, the fed-batch production of (R)-o-chloromandelic acid was attained with 32.2 g/L productivity within 22 h, in 82.4% yield and 93.1% ee. With o-chlorobenzaldehyde and potassium cyanide as the substrates, (R)-o-chloromandelic acid was also produced in 89.5% yield and 98.6% ee.

Fenzi Cuihua published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C12H23N3S, Quality Control of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Liu, Huijun published the artcileHighly chemoselective and efficient Strecker reaction of aldehydes with TMSCN catalyzed by MgI₂ etherate under solvent-free conditions, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2019), 194(9), 933-936, database is CAplus.

Strecker reaction of various substituted aromatic aldehydes, heteroaromatic aldehydes, aliphatic aldehydes and α,β-unsaturated aldehydes with trimethylsilyl cyanide (TMSCN) was realized in the presence of 5 mol % of MgI₂ etherate in a mild, efficient and highly chemoselective manner under solvent-free conditions.

Phosphorus, Sulfur and Silicon and the Related Elements published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

McEwen, William E. published the artcileSynthetic uses of open-chain analogs of Reissert compounds, Related Products of nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (1980), 45(7), 1301-8, database is CAplus.

Open-chain analogs, RN(COR²)CHR¹CN (I, R = Ph, PhCH₂, p-ClC₆H₄, p-MeOC₆H₄, Me(CH₂)₅, cyclohexyl; R¹ = Ph, H, o-, m-, p-ClC₆H₄, 3,4-(MeO)₂C₆H₃, o-, m-MeOC₆H₄, Bu; R² = Ph, Me), of Reissert compounds are obtained by reaction of R¹CH(OH)CN with RNH₂, the resulting aminonitriles, RNHCHR¹CN, then being acylated. Hydrofluoroborate salts, II, of I, are prepared by reaction with fluoroboric acid in HOAc. The salts, II, undergo 1,3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with Et acrylate to give a different type of substituted pyrrole, the initial step in this instance being a Diels-Alder reaction. Thus, addition of MeO₂CCCCO₂Me to II (R¹ = R² = Ph) gave III (R = Ph, m-ClC₆H₄, p-MeOC₆H₄, PhCH₂); and addition of H₂C:CHCO₂Et to II (R = R¹ = R² = Ph) gave IV. I also undergo base-catalyzed reactions, such as alkylation with R⁵Br to provide R²CONRCR¹R⁵CN (R⁵ = PhCH₂, Bu, α-naphthylmethyl, R-R² = as above), which, in turn, undergo cleavage reactions in ethanolic alkali to give ketones R¹R⁵CO. A conjugate addition reaction of the anion BzNPhC^–PhCN (V) to Me acrylate to give, after subsequent steps, VI was demonstrated. α-Anilino ketones, PhNHCHRCOR¹, result when the anion V is treated with aldehydes, the initial reaction mixtures being subjected to subsequent alk. hydrolysis. Finally, N-benzyl Reissert analogs give desoxybenzoins plus benzonitriles on treatment with NaH in THF.

Journal of Organic Chemistry published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wang, Hualei published the artcileProtein engineering of a nitrilase from Burkholderia cenocepacia J2315 for efficient and enantioselective production of (R)-o-chloromandelic acid, Related Products of nitriles-buliding-blocks, the publication is Applied and Environmental Microbiology (2015), 81(24), 8469-8477, database is CAplus and MEDLINE.

The nitrilase-mediated pathway has significant advantages in the production of optically pure aromatic α-hydroxy carboxylic acids. However, low enantioselectivity and activity are observed on hydrolyzing o-chloromandelonitrile to produce optically pure (R)-o-chloromandelic acid. A protein engineering approach was successfully used to enhance the performance of nitrilase obtained from Burkholderia cenocepacia strain J2315 (BCJ2315) in hydrolyzing o-chloromandelonitrile. Four hot spots (T49, I113, Y199, and T310) responsible for the enantioselectivity and activity of BCJ2315 were identified by random mutagenesis. An effective double mutant (I113M/Y199G [encoding the replacement of I with M at position 113 and Y with G at position 199]), which demonstrated remarkably enhanced enantioselectivity (99.1% enantiomeric excess [ee] compared to 89.2% ee for the wild type) and relative activity (360% of the wild type), was created by two rounds of site saturation mutagenesis, first at each of the four hot spots and subsequently at position 199 for combination with the selected beneficial mutation I113M. Notably, this mutant also demonstrated dramatically enhanced enantioselectivity and activity toward other mandelonitrile derivatives and, thus, broadened the substrate scope of this nitrilase. Using an Et acetate-water (1:9) biphasic system, o-chloromandelonitrile (500 mM) was completely hydrolyzed in 3 h by this mutant with a small amount of biocatalyst (10 g/L wet cells), resulting in a high concentration of (R)-o-chloromandelic acid with 98.7% ee, to the authors’ knowledge the highest ever reported. This result highlights a promising method for industrial production of optically pure (R)-o-chloromandelic acid. Insight into the source of enantioselectivity and activity was gained by homol. modeling and mol. docking experiments

Applied and Environmental Microbiology published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C18H10, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sun, Huihui published the artcileCloning, purification and evaluation of the enzymatic properties of a novel arylacetonitrilase from Luminiphilus syltensis NOR5-1B: a potential biocatalyst for the synthesis of mandelic acid and its derivatives, Category: nitriles-buliding-blocks, the publication is Biotechnology Letters (2015), 37(8), 1655-1661, database is CAplus and MEDLINE.

Objective: To examine nitrilase-mediated hydrolysis of nitriles to produce optically pure α-hydroxycarboxylic acids. Results: A novel nitrilase, GPnor51, from Luminiphilus syltensis NOR5-1B was discovered by genomic data mining. It could hydrolyze racemic o-chloromandelonitrile to (R)-o-chloromandelic acid with high enantioselectivity (ee 98.2 %). GPnor51 was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties studied. GPnor51 had a broad substrate acceptance toward various nitriles with structure diversity. It was an arylacetonitrilase that uses arylacetonitriles as optimal substrates. The V_max and K_m of GPnor51 towards o-chloromandelonitrile were 1.9 μmol min^-1 mg^-1 protein and 0.38 mM, resp. GPnor51 also demonstrated high enantioselectivity toward mandelonitrile and other substituted mandelonitrile. Conclusion: This enzyme has a great potential for com. production of optically pure (R)-mandelic acid and its derivatives

Biotechnology Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C10H13NO2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sun, Huihui published the artcileExpression, characterization of a novel nitrilase PpL19 from Pseudomonas psychrotolerans with S-selectivity toward mandelonitrile present in active inclusion bodies, Name: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Biotechnology Letters (2016), 38(3), 455-461, database is CAplus and MEDLINE.

Objectives: To identify a novel nitrilase with S-selectivity toward mandelonitrile that can produce (S)-mandelic acid in one step. Results: A novel nitrilase PpL19 from Pseudomonas psychrotolerans L19 was discovered by genome mining. It showed S-selectivity with an enantiomeric excess of 52.7% when used to hydrolyze (R,S)-mandelonitrile. No byproduct was observed PpL19 was overexpressed in Escherichia coli BL21 (DE3) and formed inclusion bodies that were active toward mandelonitrile and stable across a broad range of temperature and pH. In addition, PpL19 hydrolyzed nitriles with diverse structures; arylacetonitriles were the optimal substrates. Homol. modeling and docking studies of both enantiomers of mandelonitrile in the active site of nitrilase PpL19 shed light on the enantioselectivity. Conclusions: A novel nitrilase PpL19 from P. psychrotolerans L19 was mined and distinguished from other nitrilases as it was expressed as an active inclusion body and showed S-selectivity toward mandelonitrile.

Biotechnology Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C10H9NO, Name: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts