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

Description

(R)-ALPHA-CYANOBENZYL ACETATE, also known as (R)-α-Acetoxyphenylacetonitrile, is an organic compound with the molecular formula C10H9NO2. It is a chiral molecule, which means it has a non-superimposable mirror image, and is characterized by the presence of a cyano group (-CN) and an acetate group. (R)-ALPHA-CYANOBENZYL ACETATE is of interest in the field of organic chemistry and pharmaceutical research due to its unique structure and potential applications.

Uses

Used in Chemical Synthesis:
(R)-ALPHA-CYANOBENZYL ACETATE is used as a model compound for [chemical synthesis] for [its unique structure and reactivity]. It is particularly useful in the synthesis of secondary amides through an aryl?N-addition reaction to the -CN group of nitriles. This process can be promoted by iodine or t-BuONO, which facilitates the formation of the desired products.
Used in Pharmaceutical Research:
(R)-ALPHA-CYANOBENZYL ACETATE is used as a key intermediate in the development of new pharmaceutical compounds for [various therapeutic applications]. Its unique structure and reactivity make it a valuable building block for the synthesis of novel drug candidates, potentially leading to the discovery of new treatments for various diseases and conditions.
Used in Research and Development:
(R)-ALPHA-CYANOBENZYL ACETATE is used as a research tool in [academic and industrial laboratories] for [exploring new reaction pathways and understanding the fundamental chemistry of nitriles and amides]. Its use in research can lead to the development of new synthetic methods, improved reaction conditions, and a deeper understanding of the underlying chemical processes.

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

• 18942-90-0 2-nitro-1-phenylethyl acetate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 140-29-4 phenylacetonitrile 
• 631-57-2 Acetyl cyanide 
• 100-52-7 benzaldehyde 
• 2408-36-8 lithium cyanide 
• 75-36-5 acetyl chloride 
• 151-50-8 potassium cyanide 
• 613-90-1 benzoyl cyanide 
• 64-19-7 acetic acid 
• 7677-24-9 trimethylsilyl cyanide 
• 581-55-5 benzylidene 1,1-diacetate 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 108-24-7 acetic anhydride 

Downstream Products

• 40060-76-2 (±)-phenyl(1H-tetrazol-5-yl)methanol 
• 4442-85-7 2-cyclohexylethylamine 
• 64-04-0 phenethylamine 
• 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 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 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 

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.

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

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.