Benzoyl cyanide

Structural formula
General
Surname	Benzoyl cyanide
other names	Phenylglyoxylonitrile
Molecular formula	C 8 H 5 NO
Brief description	colorless to yellowish solid with a pungent odor
External identifiers / databases
EC number	210-359-7
ECHA InfoCard	100.009.419
PubChem	11953
Wikidata	Q15632897
properties
Molar mass	131.13 g mol −1
Physical state	firmly
density	1.11 g cm −3
Melting point	30-32 ° C
boiling point	206 ° C
Vapor pressure	1.9 mbar (50 ° C)
solubility	decomposes in water
safety instructions
H and P phrases	H: 301 + 311-332-314-400
	P: 273-280-301 + 330 + 331-304 + 340-305 + 351 + 338-310
Toxicological data	37.6 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benzoyl cyanide is a chemical compound from the group of nitriles . Analogously to the carboxylic acid halides , the compound can be used as a carboxylic acid cyanide , i.e. H. can be understood as the cyanide of benzoic acid .

Occurrence

Benzoyl cyanide occurs naturally as a poison from some bipeds .

Extraction and presentation

Benzoyl cyanide can be obtained by reacting benzoyl chloride with copper (I) cyanide .

properties

Benzoyl cyanide is a colorless to yellowish solid with a pungent odor that decomposes in water to form phenylglyoxylic acid ( benzoylformic acid ) .

use

Benzoyl cyanide is used as an intermediate in the manufacture of other chemical compounds (e.g. crop protection products ). It serves as a reagent for selective acylation of amino compounds.

safety instructions

The vapors of benzoyl cyanide can form an explosive mixture with air ( flash point approx. 74 ° C, ignition temperature approx. 500 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on benzoyl cyanide in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ ^a ^b Datasheet Benzoyl cyanide, 98% from Sigma-Aldrich , accessed on March 9, 2013 ( PDF ).
↑ Thomas Eisner, Jerrold Meinwald, National Academy of Sciences (US): Chemical ecology: the chemistry of biotic interaction . National Academies, 1995, pp. 30 ( limited preview in Google Book search).
↑ TS Oakwood, CA Weisgerber: Benzoyl Cyanide In: Organic Syntheses . 24, 1944, p. 14, doi : 10.15227 / orgsyn.024.0014 ; Coll. Vol. 3, 1955, p. 112 ( PDF ).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on benzoyl cyanide in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[Sigma-2] Datasheet Benzoyl cyanide, 98% from Sigma-Aldrich , accessed on March 9, 2013 ( PDF ).

[Thomas_Eisner,_Jerrold_Meinwald,_National_Academy_of_Sciences_(U.S.)-3] Thomas Eisner, Jerrold Meinwald, National Academy of Sciences (US): Chemical ecology: the chemistry of biotic interaction . National Academies, 1995, pp. 30 ( limited preview in Google Book search).

[Organic_Syntheses-4] TS Oakwood, CA Weisgerber: Benzoyl Cyanide In: Organic Syntheses . 24, 1944, p. 14, doi : 10.15227 / orgsyn.024.0014 ; Coll. Vol. 3, 1955, p. 112 ( PDF ).