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Phenacyl chloride

Despite the letters CN, this chemical does not contain a cyanide component.
Phenacyl chloride
Skeletal formula
Ball-and-stick model
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IUPAC name
2-chloro-1-phenylethanone
Other names
alpha-Chloroacetophenone, 2-Chloroacetophenone, Chloromethyl phenyl ketone, Phenyl chloromethyl ketone
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532-27-4 7pxY
ChEMBL ChEMBL105712 7pxN
ChemSpider 10303 7pxN
Jmol-3D images Image
PubChem Template:Chembox PubChem/format
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C8H7ClO
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Appearance white to gray crystalline solid[1]
Odor pungent and irritating[1]
Density 1.324 g/cm3
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insoluble
Vapor pressure 0.005 mmHg (20°C)[1]
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SDS []
Main hazards Combustible[1]
EU classification Toxic T
NFPA 704

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US health exposure limits (NIOSH):

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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2]

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:[3]

500px

Riot control agent

It was investigated, but not used, during the First and Second World Wars.

Because of its significantly greater toxicity,[4] it has largely been supplanted by CS gas. Even though CN is still supplied to paramilitary and police forces in a small pressurized aerosol known as “Mace” or tear gas, its use is falling as pepper spray both works 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, In the United States, 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 genericized trademark).[citation needed]

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.[4] More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis.[2]

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.[5]

References

  1. ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0119". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ a b Treudler, R.; Tebbe, B.; Blume-Peytavi, U.; Krasagakis, K.; Orfanos, C. E. (1999). "Occupational contact dermatitis due to 2-chloracetophenone tear gas". British Journal of Dermatology 140 (3): 531–534. PMID 10233281. doi:10.1046/j.1365-2133.1999.02724.x.  edit
  3. ^ Levin, N.; Hartung, W. H. (1955). "ω-Chloroisonitrosoacetophenone". Org. Synth. ; Coll. Vol. 3, p. 191 
  4. ^ a b Ballantyne, B.; Swanston, D. W. (1978). "The comparative acute mammalian toxicity of 1-chloroacetophenone (CN) and 2-chlorobenzylidene malononitrile (CS)". Archives of Toxicology 40 (2): 75–95. PMID 350195. doi:10.1007/BF01891962. 
  5. ^ Blain, P. G. (2003). "Tear Gases and Irritant Incapacitants: 1-Chloroacetophenone, 2-Chlorobenzylidene Malononitrile and Dibenz[b,f]-1,4-Oxazepine". Toxicological Reviews 22 (2): 103–110. PMID 15071820. doi:10.2165/00139709-200322020-00005. 


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