Bromobenzyl cyanide

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Structural formula
(±) -Bromobenzyl cyanide: structural formulas of both enantiomers
( R ) shape (left) and ( S ) shape (right)
General
Surname Bromobenzyl cyanide
other names
  • BBC
  • CA
  • Bromophenylacetonitrile
  • Cyanogen bromide benzene
  • Phenylbromocyanomethane
  • ( R ) -Bromobenzyl Cyanide
  • ( S ) -Bromobenzyl cyanide
  • ( RS ) -Bromobenzyl Cyanide
  • (±) -Bromobenzyl cyanide
Molecular formula C 8 H 6 BrN
Brief description

yellowish solid

External identifiers / databases
CAS number 5798-79-8
EC number 227-348-8
ECHA InfoCard 100,024,863
PubChem 22044
Wikidata Q425589
properties
Molar mass 196.05 g mol −1
Physical state

solid, technically produced often also liquid

density

1.54 g cm −3

Melting point

29 ° C

boiling point

242 ° C

solubility
safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 300 + 310 + 330-315-319
P: 233-260-261-264-270-271-280-301 + 312-302 + 352-304 + 340-305 + 351 + 338-312-321-330-332 + 313-337 + 313-340-362-403 + 233-405Template: P-phrases / maintenance / more than 20 phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bromobenzyl cyanide is a chemical compound that is very irritating to the eyes . It was used as a chemical warfare agent.

Chemically, bromobenzyl cyanide is a stable compound; it is very resistant to hydrolysis . Pure bromobenzyl cyanide forms whitish to pale pink crystals , the technical product is a brown, oily liquid. It smells fruity. Because of its low volatility, bromobenzyl cyanide has a long duration of action. Its thermal instability and its detonation instability are disadvantageous. When heated, hydrogen cyanide can only develop in extreme cases . Bromobenzyl cyanide was used by the American side (CA, BBC) and the French side (Camite) at the end of the First World War . It is absorbed through the mucous membranes, eyes or breathing and leads to reddening of the skin and itching. Bromobenzyl cyanide is a strong eye irritant, even a concentration of 5 mg / m³ air is unbearable within a minute; the ICt 50 (concentration of the warfare agent which makes 50% of the exposed persons incapable of fighting) is 80–90 mg / m³ air in one minute of exposure. Immediate rinsing of the eye is imperative.

Bromobenzyl cyanide contains a stereocenter and is therefore chiral . The racemic bromobenzyl cyanide is a 1: 1 mixture of ( R ) -bromobenzyl cyanide and the mirror image of ( S ) -bromobenzyl cyanide.

See also

Individual evidence

  1. ↑ a b c d e f Entry on ALPHA-BROMOBENZYL CYANIDE in the Hazardous Substances Data Bank , accessed on January 1, 2008.
  2. ↑ Entry on bromobenzyl cyanide at TCI Europe, accessed on February 16, 2020.
  3. ↑ Bromobenzyl cyanide at Florochem. Retrieved March 14, 2020 .
  4. ^ National Academy of Sciences, National Research Council , Chemical-Biological Coordination Center, Review. Volume 5, p. 32, 1953.
  5. ↑ a b Entry on bromophenylacetonitrile in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 28, 2019.
  6. ^ National Defense Research Committee , Office of Scientific Research and Development, Progress Report. Vol. ND, Crc-132, August 1942.
  7. ^ Franke, S. et al .: Textbook of Military Chemistry , Volume 1, 2nd Edition, Military Publishing House of the GDR, Berlin (East), 1977.