Phenacyl chloride

Phenacyl chloride
IUPAC name 2-chloro-1-phenylethanone
Identifiers
CAS number	532-27-4 Y
PubChem	10757
ChemSpider	10303 N
ChEMBL	CHEMBL105712 N
Jmol-3D images	Image 1
SMILES c1ccc(cc1)C(=O)CCl
InChI InChI=InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
Properties
Molecular formula	C8H7ClO
Molar mass	154.59 g mol−1
Melting point	54-56 °C, 327-329 K, 129-133 °F
Hazards
MSDS	Oxford MSDS
EU classification	T
N chloride (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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 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 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).

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

1. ^ Nathan Levin and Walter H. Hartung (1955), "ω-Chloroisonitrosoacetophenone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0191 ; Coll. Vol. 3: 191 
2. ^ Blain, P. G. (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. http://www.ingentaconnect.com/content/adis/txr/2003/00000022/00000002/art00005. 

This article related to weaponry is a stub. You can help Wikipedia by expanding it.v · Categories: Riot control agents Lachrymatory agents Weapon stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем написать реферат Chloroacetamide N(4)-Chloroacetylcytosine arabinoside Look at other dictionaries: phenacyl chloride — noun : chloroacetophenone …   Useful english dictionary Phenacyl — In organic chemistry, a phenacyl group is an aromatic functional group that consists of a phenyl group attached to an acyl group. A molecule containing a phenacyl group has the formula RCH2(CO)C6H5 and the structure shown to the right. Here, R… …   Wikipedia Chloroacetyl chloride — Chloroacetyl chloride …   Wikipedia Munster Training Area — emblem …   Wikipedia Lachrymatory agent — A lachrymatory agent or lachrymator (from lacrima meaning a tear in Latin) (commonly referred to as tear gas) is a chemical compound that stimulates the corneal nerves in the eyes to cause tearing, pain, and even temporary blindness. Common… …   Wikipedia Chlorure de chloroacétyle — Général …   Wikipédia en Français Oxime — An oxime is a chemical compound belonging to the imines, with the general formula R1R2C=NOH, where R1 is an organic side chain and R2 may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O substituted oximes form a… …   Wikipedia Alkyl nitrites — s (R NO2).The first few members of the series are volatile liquids; methyl nitrite and ethyl nitrite are gaseous at room temperature and pressure. The compounds have a distinctive fruity odor. Another frequently encountered nitrite is amyl… …   Wikipedia CN gas — Chembox new Name = CN gas ImageFile = Chloroacetophenone.svg ImageSize = 106px ImageName = CN gas IUPACName = 2 chloro 1 phenylethanone Section1 = Chembox Identifiers CASNo = 532 27 4 SMILES = c1ccc(cc1)C(=O)CCl Section2 = Chembox Properties… …   Wikipedia Non-lethal weapon — Pepper spray demonstration Non lethal weapons, also called less lethal weapons, less than lethal weapons, non deadly weapons, compliance weapons, or pain inducing weapons are weapons intended to be less likely to kill a living target than are… …   Wikipedia 18+ © Academic, 2000-2025 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”