// Workers AI · dad joke modeIs Bromobenzyl cyanide a bond-ing experience?
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| Names | |
|---|---|
| IUPAC name
(RS)-2-bromo-2-phenylacetonitrile | |
| Other names
α-bromobenzyl cyanide | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.024.863 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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) |
| 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] | |
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| Warning | |
| H302, H315, H319, H335 | |
| 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).
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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]
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]
Use against protestors in 2024
[edit]Despite it being described as obsolete, Georgian authorities appeared to have used camite in November 2024 against civil protestors in Tbilisi, adding it to the water in a water cannon aimed at the people, according to a BBC News investigation.[4]
Applications
[edit]An application for bromobenzyl cyanide is in Hoch's synthesis of diphenylacetonitrile.[7]
See also
[edit]References
[edit]- ↑ "Bromobenzyl Cyanide". pubchem.ncbi.nlm.nih.gov. Retrieved 25 December 2025.
- ↑ 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.
- ↑ "Physical properties of Brombenzyl(sic) cyanide (C.A.)". Chemical Warfare Bulletin. 12 (312): 8. 1926 – via babel.hathitrust.org.
- 1 2 Hudson, Max; Marocico, Oana; Buckley, Sarah (November 30, 2025). "WW1 toxic compound sprayed on Georgian protesters, BBC evidence suggests". BBC. Retrieved November 30, 2025.
Georgia's authorities used a World War One-era chemical weapon to quell anti-government protesters last year, evidence gathered by the BBC suggests.
- ↑ Sartori, Mario (1939). The War Gases. D. Van Nostrand. p. 196 – via archive.org.
- ↑ "Chapter VII Riot Control Agents". FM 8-9 NATO Handbook on the Medical Aspects of NBC Operation AMedP-6(B). FAS.org.
- ↑ "Diphenylacetonitrile". Organic Syntheses. 28: 55. 1948. doi:10.15227/orgsyn.028.0055.
External links
[edit]- "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.