View source for Phenacyl chloride

__NOTOC__
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 296402074
|   Name =
|   ImageFile = Chloroacetophenone.svg
|   ImageSize = 180px
|   ImageName = Skeletal formula
|   ImageFile1 = Phenacyl-chloride-3D-balls.png
|   ImageSize1 = 180px
|   ImageName1 = Ball-and-stick model
|   IUPACName = 2-chloro-1-phenylethanone
| Section1 = {{Chembox Identifiers
|   CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 532-27-4
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 105712
|  PubChem = 10757
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 10303
|  InChI = InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
|   SMILES = c1ccc(cc1)C(=O)CCl
  }}
| Section2 = {{Chembox Properties
|   C = 8 |H = 7 | O = 1 | Cl = 1
|   Density = 1.324 g/cm<sup>3</sup>
|   MeltingPtCL = 54
|   MeltingPtCH = 56
|   BoilingPtC = 244.5
|   Solubility = insoluble
  }}
| Section7 = {{Chembox Hazards
|   EUClass = {{Hazchem T}}
|   MainHazards =
|   FlashPt = 88 °C
|   Autoignition =
|   NFPA-H = 3
|   NFPA-F = 1
|   NFPA-R = 0
|   NFPA-O =
|   ExternalMSDS = [http://msds.chem.ox.ac.uk/CH/2-chloroacetophenone.html Oxford MSDS]
  }}
}}
{{SI}}
{{CMG}}
==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:<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==
It was investigated, but not used, during the [[World War I|First]] and [[Second World War]]s.

Because of its significantly greater toxicity,<ref name="xl">{{Cite journal | last1 = Ballantyne | first1 = B. | last2 = Swanston | first2 = D. W. | doi = 10.1007/BF01891962 | title = The comparative acute mammalian toxicity of 1-chloroacetophenone (CN) and 2-chlorobenzylidene malononitrile (CS) | journal = Archives of Toxicology | volume = 40 | issue = 2 | pages = 75–95 | year = 1978 | pmid =  350195| pmc = }}</ref> 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 (spray)|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 paper]]s (a phenomenon known as a [[genericized trademark]]).{{fact|date=July 2012}}

Like CS gas, this compound irritates the [[mucous membrane]]s (oral, nasal, [[conjunctiva]]l and [[tracheobronchial]]). Sometimes it can give rise to more generalized reactions such as [[fainting|syncope]], temporary loss of balance and orientation.<ref name="xl" /> More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent [[dermatitis]].<ref>{{cite doi|10.1046/j.1365-2133.1999.02724.x}}</ref>

At high concentrations CN has caused [[corneal epithelium|corneal epithelial]] damage and [[chemosis]]. It has also accounted for at least five deaths, which have resulted from [[pulmonary injury]] and/or [[asphyxia]].<ref>{{ cite journal | last = Blain | first = P. G. | title = Tear Gases and Irritant Incapacitants: 1-Chloroacetophenone, 2-Chlorobenzylidene Malononitrile and Dibenz&#91;b,f&#93;-1,4-Oxazepine | journal = Toxicological Reviews | volume = 22 | issue = 2 | pages = 103–110 | year = 2003 | pmid = 15071820 | url = http://www.ingentaconnect.com/content/adis/txr/2003/00000022/00000002/art00005 }}</ref>

==References==
{{reflist}}

{{Chemical warfare}}

{{DEFAULTSORT:Phenacyl Chloride}}
[[Category:Riot control agents]]
[[Category:Lachrymatory agents]]


{{weapon-stub}}

[[ar:غاز سي إن]]
[[de:Ω-Chloracetophenon]]
[[es:Gas CN]]
[[fa:کلرید فناسیل]]
[[fr:Chloroacétophénone]]
[[it:Gas CN]]
[[kk:Хлорацетофенон]]
[[lt:Chloracetofenonas]]
[[nl:Chlooracetofenon]]
[[ja:クロロアセトフェノン]]
[[pl:Chloroacetofenon]]
[[ru:Хлорацетофенон]]
[[sl:Kloracetofenon]]
[[sv:Fenacylklorid]]
[[th:แก๊สซีเอ็น]]
[[zh:2-氯苯乙酮]]