138145-61-6

Basic information

• Product Name: 3-benzoyloxy-4-cyanobutanoic acid
• Synonyms: 3-benzoyloxy-4-cyanobutanoic acid
• CAS NO: 138145-61-6
• Molecular Formula: C₁₂H₁₁NO₄
• Molecular Weight: 0
• Mol File: 138145-61-6.mol

Chemical Properties

• Boiling Point: 470.5°Cat760mmHg
• Flash Point: 238.3°C
• Appearance: /
• Density: 1.283g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 3-benzoyloxy-4-cyanobutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzoyloxy-4-cyanobutanoic acid(138145-61-6)
• EPA Substance Registry System: 3-benzoyloxy-4-cyanobutanoic acid(138145-61-6)

Safety Data

• Hazardous Substances Data: 138145-61-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H11NO4/c13-7-6-10(8-11(14)15)17-12(16)9-4-2-1-3-5-9/h1-5,10H,6,8H2,(H,14,15)

Upstream product

• 98-88-4 benzoyl chloride 
• 13880-89-2 3-hydroxyglutaronitrile 
• 138145-58-1 3-O-(benzoyl)-glutaronitrile 

Downstream Products

• 147963-59-5 Benzoic acid (S)-2-cyano-1-[((S)-1-naphthalen-1-yl-ethylcarbamoyl)-methyl]-ethyl ester 
• 147963-59-5 Benzoic acid (S)-2-cyano-1-[((R)-1-naphthalen-1-yl-ethylcarbamoyl)-methyl]-ethyl ester 
• 147028-56-6 (S)-(+)-methyl-(3-O--4-cyano)-butanoate 

Relevant articles and documents

Stereoselective Hydrolysis of Nitriles and Amides Under Mild Conditions Using a Whole Cell Catalyst

An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid.A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84percent.Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.

Enzymic Hydrolysis of Prochiral Dinitriles

A series of prochiral 3-hydroxyglutaronitrile derivatives 1-5 has been enzymically hydrolysed to the corresponding nitrile-carboxylic acids 1b-5b with enantiomeric excesses ranging from 22-84percent.In all cases the products were of the (S)-configuration.

Microbial Hydrolysis of 3-Substituted Glutaronitriles

Rhodococcus butanica ATCC 21197 preferentially hydrolyzed pro-S cyano group of 3-substituted glutaronitriles with an aromatic ring.A product with high e.e. (>99 percent) was obtained from 3-benzoyloxy derivative.