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Benzoyl cyanide

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Benzoyl cyanide Basic information

Product Name:
Benzoyl cyanide
Synonyms:
  • BENZOYL CYANIDE
  • PHENYLGLYOXYLONITRILE
  • alpha-oxophenylacetonitrile
  • Benzoyl cyanide, 95% 25GR
  • Benzeneacetonitrile,a-oxo-
  • Benzoyl nitrile
  • Glyoxylonitrile, phenyl-
  • Oxo(phenyl)acetonitrile
CAS:
613-90-1
MF:
C8H5NO
MW:
131.13
EINECS:
210-359-7
Mol File:
613-90-1.mol
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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)
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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
10
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29269095

MSDS

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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 Preparation Products And Raw materials

Raw materials

Preparation Products

Benzoyl cyanideSupplier

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