179694-34-9

Basic information

• Product Name: Benzonitrile, 4-(2R)-2-oxiranyl-
• Synonyms: Benzonitrile, 4-(2R)-oxiranyl-(9CI); Benzonitrile, 4-oxiranyl-, (R)-
• CAS NO: 179694-34-9
• Molecular Formula: C9H7 N O
• Molecular Weight: 145.161
• Mol File: 179694-34-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-(2R)-2-oxiranyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(2R)-2-oxiranyl-(179694-34-9)
• EPA Substance Registry System: Benzonitrile, 4-(2R)-2-oxiranyl-(179694-34-9)

Safety Data

• Hazardous Substances Data: 179694-34-9(Hazardous Substances Data)

Usage

General Description

Benzonitrile, 4-(2R)-2-oxiranyl- is a chemical compound with the molecular formula C9H17NO. It is also known as (2R)-4-(oxiran-2-yl)benzonitrile. Benzonitrile, 4-(2R)-2-oxiranyl- is a nitrile derivative and contains a benzene ring with a nitrile group and a 2R-2-oxiranyl group. It is used in organic synthesis and as a building block for the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. The 2R-2-oxiranyl group in this compound makes it a chiral molecule, which can have different biological and chemical properties compared to its enantiomer.

Upstream product

• 52695-39-3 4-oxiran-2-ylbenzonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 20099-89-2 4-Cyanophenacyl bromide 
• 85554-13-8 (±)-4-(2-bromo-1-hydroxyethyl)benzonitrile 
• 173727-98-5 (R)-1-(4-cyanophenyl)-1,2-ethanediol 
• 1097210-78-0 C₁₆H₁₅NO₄S 
• 16508-11-5 4-(2-chloro-1-hydroxy-ethyl)-benzonitrile 
• 3435-51-6 4-ethenylbenzonitrile 

Downstream Products

• 1097210-79-1 C₂₃H₂₈N₂O₃ 
• 603125-44-6 sodium 4-((7S)-7-{[(2R)-2-(4-cyanophenyl)-2-hydroxyethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenyl)benzoate 
• 173727-98-5 (R)-1-(4-cyanophenyl)-1,2-ethanediol 
• 213479-94-8 (S)-1-(4-cyanophenyl)-1,2-ethanediol 

Relevant articles and documents

The Stereoselective Oxidation of para-Substituted Benzenes by a Cytochrome P450 Biocatalyst

The serine 244 to aspartate (S244D) variant of the cytochrome P450 enzyme CYP199A4 was used to expand its substrate range beyond benzoic acids. Substrates, in which the carboxylate group of the benzoic acid moiety is replaced were oxidised with high activity by the S244D mutant (product formation rates >60 nmol.(nmol-CYP)?1.min?1) and with total turnover numbers of up to 20,000. Ethyl α-hydroxylation was more rapid than methyl oxidation, styrene epoxidation and S-oxidation. The S244D mutant catalysed the ethyl hydroxylation, epoxidation and sulfoxidation reactions with an excess of one stereoisomer (in some instances up to >98 %). The crystal structure of 4-methoxybenzoic acid-bound CYP199A4 S244D showed that the active site architecture and the substrate orientation were similar to that of the WT enzyme. Overall, this work demonstrates that CYP199A4 can catalyse the stereoselective hydroxylation, epoxidation or sulfoxidation of substituted benzene substrates under mild conditions resulting in more sustainable transformations using this heme monooxygenase enzyme.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Asymmetric epoxidation of alkenes and benzylic hydroxylation with P450tol monooxygenase from Rhodococcus coprophilus TC-2

P450tol monooxygenase was discovered as a unique and highly enantioselective enzyme for asymmetric epoxidation of some terminal alkenes containing electron-withdrawing groups and benzylic hydroxylation of several ethylbenzenes giving the corresponding useful and valuable products, such as (R)-2- and 3-substituted styrene oxides, (S)-4-substituted styrene oxides, and (S)-benzylic alcohols, in high ee.