Bromobenzyl cyanide

Bromobenzyl cyanide (BBC), also known in the military idiom as camite, is an obsolete lachrymatory agent^[2] introduced in World War I by the Allied Powers, being a standard agent, along with chloroacetophenone, adopted by the Chemical Warfare Service.^[3] It was thought to have been phased out in the 1930s, but has allegedly seen use in 2024, when authorities in the Republic of Georgia are said to have used it to quell anti-government protests. ^[4]

Quick facts Names, Identifiers ...

Bromobenzyl cyanide

Names
IUPAC name (RS)-2-bromo-2-phenylacetonitrile
Other names α-bromobenzyl cyanide
Identifiers
CAS Number	5798-79-8 Y
3D model (JSmol)	Interactive image
ChemSpider	20715 N
ECHA InfoCard	100.024.863
PubChem CID	22044
UNII	7JP1R2F6C6 Y
CompTox Dashboard (EPA)	DTXSID50871146
InChI InChI=1S/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H N Key: XUHFBOUSHUEAQZ-UHFFFAOYSA-N N InChI=1/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H Key: XUHFBOUSHUEAQZ-UHFFFAOYAJ
SMILES C1=CC=C(C=C1)C(C#N)Br
Properties
Chemical formula	C8H6BrN
Molar mass	196.04 g mol−1
Appearance	Pale yellow crystals
Odor	odor of soured fruit
Density	1.539 g/cm3
Melting point	29 °C (84 °F; 302 K)
Boiling point	242 °C (468 °F; 515 K)
Solubility in water	slightly soluble
Solubility	freely soluble in alcohol, ether, acetone, and chloroform soluble in phosgene, chloropicrin and benzyl cyanide
Vapor pressure	0.012 mmHg (20 °C)
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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When implemented in World War I, it revolutionized the use of tear agents due to its extreme potency and great persistence.^[5] Bromobenzyl cyanide has been described as too toxic for use as a non-lethal crowd control agent.^[6]