Bromobenzyl cyanide

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
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

Bromobenzyl cyanide (BBC), also known in the military idiom as camite (CA), is an obsolete lachrymatory agent ^[1] introduced in World War I by the Allied Powers, being a standard agent, along with chloroacetophenone, adopted by the CWS. ^[2] When implemented in World War I, it revolutionized the use of tear agents due to its extreme potency and great persistence. ^[3] BBC is toxic like chlorine gas. ^[4]

An application for bromobenzyl cyanide is in Hoch's synthesis of diphenylacetonitrile. ^[5]

See also

• Chloroacetophenone
• CR gas
• CS gas
• Lachrymatory agent

References

1. Davies, W; MacLaren, J. A (1951). "330. The reaction of α-bromobenzyl cyanide with ethyl xanthamidate (thioncarbamate)". J. Chem. Soc.: 1434–1437. doi:10.1039/JR9510001434.
2. Chemical Warfare Bulletin. Vol 12. p 312
3. Sartori, Mario (1939). The War Gases. D. Van Nostrand. p. 196.
4. AMOS A. FRIES and CLARENCE J. WEST. CHEMICAL WARFARE - First Edition. p 142-143
5. "DIPHENYLACETONITRILE". Organic Syntheses. 28: 55. 1948. doi:10.15227/orgsyn.028.0055.

External links

• "Chapter VII Riot Control Agents". FM 8-9 NATO Handbook On the Medical Aspects of NBC Operation AMedP-6(B). FAS.org.
• "Major Chemical Weapons Introductions in World War I". CBWInfo.com. Archived from the original on 2010-09-19.