Benzoyl cyanide Chemical Properties

Melting point:

28-31 °C(lit.)

Boiling point:

206 °C(lit.)

Density 

1.106 g/mL at 25 °C(lit.)

refractive index 

1.4700 (estimate)

Flash point:

184 °F

solubility 

soluble in Methanol

form 

powder to lump to clear liquid

color 

White or Colorless to Light yellow

Water Solubility 

slihtly soluble, decomposes

BRN 

1072101

CAS DataBase Reference

613-90-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneacetonitrile, «alpha»-oxo-(613-90-1)

EPA Substance Registry System

Benzeneacetonitrile, .alpha.-oxo- (613-90-1)

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-50-34-24/25-20

Safety Statements 

36/37/39-45-61-29-26

RIDADR 

UN 3439 6.1/PG 2

WGK Germany 

3

F 

10

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29269095

MSDS

• Language:English Provider:alpha-Oxophenylacetonitrile
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Benzoyl cyanide Usage And Synthesis

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.

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%).

Definition

ChEBI: Benzoyl cyanide is an alpha-ketonitrile and an aromatic ketone. It is functionally related to a benzoic acid.

Synthesis Reference(s)

Synthetic Communications, 15, p. 849, 1985 DOI: 10.1080/00397918508063881

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.

Benzoyl cyanide(613-90-1)Related Product Information

• Benzoyl peroxide
• Benzonitrile
• Copper(I) Cyanide
• Diethylstilbestrol
• Dibenzoylmethane
• 4-Nitrobenzonitrile
• Benzamide
• p-Tolunitrile
• Chlorantraniliprole
• Ethyl benzoylacetate
• Benzoyl isothiocyanate
• Methyl benzoylformate
• HYDROGEN CYANIDE
• Dibenzoyltartaric acid
• POTASSIUM CYANIDE
• OXO-4-TRIFLUOROMETHYL-PHENYL)-ACETONITRILE
• 2-METHYLBENZOYL CYANIDE
• Benzoyl cyanide oxime~Phenylglyoxylonitrile oxime