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
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%).
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) |
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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