Phenacyl chloride
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| Names | |
|---|---|
| IUPAC name
2-chloro-1-phenylethanone
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.007.757 |
CompTox Dashboard (EPA)
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| Properties | |
| C8H7ClO | |
| Molar mass | 154.59 g·mol−1 |
| Melting point | 54-56 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenacyl chloride is a substituted acetophenone. It is a useful building block in organic chemistry. Apart from that, it has been historically used as a riot control agent, where it is designated CN.
Preparation
Phenacyl chloride is readily available commercially. It may be synthesized by the Friedel-Crafts acylation of benzene using chloroacetyl chloride, with an aluminium chloride catalyst:[1]
Riot control agent
It was investigated, but not used, during the First and Second World Wars, and was used by United States forces in Vietnam [citation needed]. Because of its greater toxicity, it has largely been supplanted by CS gas.
CN is still supplied to paramilitary and police forces in a small pressurized aerosol can known as “Mace” or tear gas. Its use has fallen by the wayside as pepper spray works faster and disperses more quickly than CN.
The term "Mace" came into being because it was the brand-name invented by one of the first American manufacturers of CN aerosol sprays. Subsequently, Mace became synonymous with tear-gas sprays in the same way that Kleenex has become strongly associated with tissue papers (a phenomenon known as a Genericised trademark).
Like CS gas, this compound irritates the mucous membranes (oral, nasal, conjunctival and tracheobronchial). Sometimes it can give rise to more generalized reactions such as syncope, temporary loss of balance and orientation. More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis.
At high concentrations CN has caused corneal epithelial damage and chemosis. It has also accounted for at least five deaths, which have resulted from pulmonary injury and/or asphyxia.[2]
References
- ^ Nathan Levin and Walter H. Hartung (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses; Collected Volumes, vol. 3, p. 191.
- ^ Blain PG (2003). "Tear gases and irritant incapacitants. 1-chloroacetophenone, 2-chlorobenzylidene malononitrile and dibenz[b,f]-1,4-oxazepine". Toxicol Rev. 22 (2): 103–10. PMID 15071820.
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