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HomeProduct name listBenzoyl cyanide

Benzoyl cyanide

Synonym(s):Phenylglyoxylonitrile

  • CAS NO.:613-90-1
  • Empirical Formula: C8H5NO
  • Molecular Weight: 131.13
  • MDL number: MFCD00001837
  • EINECS: 210-359-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-11-08 14:41:46
Benzoyl cyanide Structural

What is Benzoyl cyanide?

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.

The Uses of Benzoyl cyanide

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%).
Preparation of Benzoyl cyanide

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.

Properties of Benzoyl cyanide

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 for Benzoyl cyanide

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H300:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

Computed Descriptors for Benzoyl cyanide

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