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
Density	1.324 g/cm3
Melting point	54 to 56 °C; 129 to 133 °F; 327 to 329 K
Boiling point	244.5 °C; 472.1 °F; 517.6 K
Solubility in water	insoluble
Hazards
MSDS	Oxford MSDS
EU classification	T
Main hazards	Combustible[1]
NFPA 704	1 3 0
Flash point	88 °C; 190 °F; 361 K
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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:^[2]

Riot control agent

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

Because of its significantly greater toxicity,^[3] 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.^[3] More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis.^[4]

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