Chemical Properties
yellow to brown low melting mass. Phenylglyoxylonitrile [613-90-1], benzoyl cyanide, Mr 131.13, mp 34℃, bp 206 – 208℃ (101.3 kPa), bp 96℃ (2 kPa), bp 82℃ (1.2 kPa), n26D 1.5303, can be used for selective reactions at the carbonyl and cyano groups. It is produced from the reaction of benzoyl chloride or benzoic anhydride with sodium cyanide (or hydrogen cyanide in the presence of alkali cyanide) in practically quantitative yield with copper (I) cyanide as catalyst. Benzoyl cyanide is used as an intermediate in the synthesis of plant protection agents.
Uses
Using benzoyl cyanide as an electrophile also gives selective acylation of the 3-position, as does levulinic acid in the presence of DCC.
Benzoyl cyanide is used to study the mechanism of reduction of benzoyl cyanide in acetonitrile, N,N-dimethylformamide and acetonitrile. It undergoes hydrolysis by Rhodococcus sp. CCZU10-1 to form benzoylformic acid. Reagent for selective acylation of amino compounds.
Definition
ChEBI: Benzoyl cyanide is an alpha-ketonitrile and an aromatic ketone. It is functionally related to a benzoic acid.
Preparation
Benzoyl cyanide is prepared by treatment of benzoyl chloride with sodium cyanide under phase-transfer catalytic conditions. This process is also used to convert 4-methyl, 4-methoxy, and 4-chlorobenzoyl chlorides into the corresponding benzoyl cyanides, and similarly cinnamoyl chloride into cinnamoyl cyanide (98%).
General Description
Benzoyl cyanide is used to study the mechanism of reduction of benzoyl cyanide in acetonitrile, N,N-dimethylformamide and acetonitrile. It undergoes hydrolysis by
Rhodococcus sp. CCZU10-1 to form benzoylformic acid.
