Phenacyl chloride: Difference between revisions

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Phenacyl chloride
	Ball-and-stick model
Names
	IUPAC name 2-chloro-1-phenylethanone
Identifiers
CAS Number	532-27-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL105712 ;
ChemSpider	10303 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
PubChem CID	10757;
	InChI InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2;
	SMILES c1ccc(cc1)C(=O)CCl;
Properties
Chemical formula	C8H7ClO
Molar mass	154.59 g·mol−1
Hazards
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

VisualWikitext

Latest revision as of 17:36, 9 August 2012

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

Because of its significantly greater toxicity,^[2] 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, 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.^[2] More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis.^[3]

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.^[4]

References

↑ Template:OrgSynth
↑ ^2.0 ^2.1 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. doi:10.1007/BF01891962. PMID 350195.
↑ Template:Cite doi
↑ 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.

Template:Chemical warfare

Template:Weapon-stub

ar:غاز سي إن de:Ω-Chloracetophenon fa:کلرید فناسیل it:Gas CN kk:Хлорацетофенон lt:Chloracetofenonas nl:Chlooracetofenon sl:Kloracetofenon sv:Fenacylklorid th:แก๊สซีเอ็น

[1] Template:OrgSynth

[xl-2] 2.0 ^2.1 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. doi:10.1007/BF01891962. PMID 350195.

[3] Template:Cite doi

[4] 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.

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[2]

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@@ Line 50: / Line 50: @@
 ==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:<ref>{{OrgSynth | title = ω-Chloroisonitrosoacetophenone | author = Levin, N.; Hartung, W. H. | collvol = 3 | collvolpages = 191 | year = 1955 | prep = cv3p0191}}</ref>
-:[[File:Preparation of phenacyl chloride.png|500px]]
 ==Riot control agent==