119718-89-7

Basic information

• Product Name: (R)-ALPHA-CYANOBENZYL ACETATE
• Synonyms: (R)-ALPHA-CYANOBENZYL ACETATE;(R)-(+)-ALPHA-ACETOXYPHENYLACETONITRILE;(R)-ALPHA-ACETOXYPHENYLACETONITRILE;O-ACETYL-D-MANDELONITRILE;D-MANDELONITRILE ACETATE;(r)-α-cyanobenzyl acetate;(R)-α-Cyanobenzyl acetate, O-Acetyl-D-mandelonitrile
• CAS NO: 119718-89-7
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Product Categories: Chiral building block
• Mol File: 119718-89-7.mol
• Article Data: 119

Chemical Properties

• Boiling Point: 268 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.115 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: n20/D 1.506
• CAS DataBase Reference: (R)-ALPHA-CYANOBENZYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-ALPHA-CYANOBENZYL ACETATE(119718-89-7)
• EPA Substance Registry System: (R)-ALPHA-CYANOBENZYL ACETATE(119718-89-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3276 6.1/PG 3
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 119718-89-7(Hazardous Substances Data)

Usage

Uses

(R)-α-Acetoxyphenylacetonitrile can be used as a model compound in the iodine promoted as well as t-BuONO-assisted secondary amides synthesis via an aryl?N-addition reaction to the -CN group of nitriles.

InChI:InChI=1/C10H9NO2/c1-8(12)13-10(7-11)9-5-3-2-4-6-9/h2-6,10H,1H3/t10-/m0/s1

Upstream product

• 532-28-5 (RS)-mandelonitrile 
• 75-36-5 acetyl chloride 
• 613-90-1 benzoyl cyanide 
• 64-19-7 acetic acid 
• 143-33-9 sodium cyanide 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 108-05-4 vinyl acetate 
• 10020-96-9 (R)-Mandelonitrile 
• 123-20-6 vinyl n-butyrate 
• 119718-87-5 cyano(phenyl)methyl acetate 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 151-50-8 potassium cyanide 
• 447-61-0 2-Trifluoromethylbenzaldehyde 

Downstream Products

• 22094-21-9 2-acetoxy-2-phenylacetaldehyde 
• 10020-96-9 (R)-Mandelonitrile 
• 28549-12-4 (S)-mandelonitrile 
• 119718-88-6 O-acetyl (S)-mandelonitrile 
• 1823-91-2 1-phenylethyl cyanide 
• 7568-93-6 2-Amino-1-phenylethanol 
• 279685-83-5 (2R)-phenyl[(tetrahydropyran-2-yloxy)]acetonitrile 
• 129313-24-2 O-butyryl-(S)-2-hydroxy-2-phenylacetonitrile 
• 120390-75-2 (R)-(+)-α-<(tert-butyldimethylsilyl)oxy>-benzeneacetonitrile 
• 147329-37-1 (S)-(-)-α-<(tert-butyldimethylsilyl)oxy>benzeneacetonitrile 
• 50911-27-8 carbamoyl(phenyl)methyl acetate 
• 29071-09-8 2-acetoxy-2-phenylacetic acid 
• 611-71-2 (R)-Mandelic Acid 
• 139759-75-4 4-mesityl-2-methyl-5-phenyloxazole 

Relevant articles and documents

Combination of the Lipase-Catalysed Resolution with Mitsunobu Esterification in One Pot

A chemo-enzymatic method for the preparation of homochiral esters of 14 secondary alcohols with 100percent theoretical yields is described in one pot through two steps: the lipase-catalysed kinetic resolution followed by the Mitsunobu esterification of the free alcohol enantiomer in situ in the resolution mixture.Mathematical equations which link the enzymatic and chemical steps were derived, resulting in an enantioconvergent synthetic tool for the preparation of chiral intermediates.

A High-Throughput Screening Method for the Directed Evolution of Hydroxynitrile Lyase towards Cyanohydrin Synthesis

Chiral cyanohydrins are useful intermediates in the pharmaceutical and agricultural industries. In nature, hydroxynitrile lyases (HNLs) are a kind of elegant tool for enantioselective hydrocyanation of carbonyl compounds. However, currently available methods for demonstrating hydrocyanation are still stalled at precise, but low-throughput, GC or HPLC analyses. Herein, we report a chromogenic high-throughput screening (HTS) method that is feasible for the cyanohydrin synthesis reaction. This method was highly anti-interference and sensitive, and could be used to directly profile the substrate scope of HNLs either in cell-free extract or fermentation clear broth. This HTS method was also validated by generating new variants of PcHNL5 that presented higher catalytic efficiency and stronger acidic tolerance in variant libraries.

Palladium-catalyzed C-H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles

An efficient and straightforward protocol for the assembly of the pharmaceutically and biologically valuable oxazole skeleton is achieved for the first time from readily available simple arenes and functionalized aliphatic nitriles. This transformation in