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2-Chloroacetophenone

Phenacyl chloride
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2-Chloro-1-phenylethan-1-one
Other names
2-Chloro-1-phenylethanone
alpha-Chloroacetophenone
2-Chloroacetophenone
Chloromethyl phenyl ketone
Phenyl chloromethyl ketone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.757
PubChem CID
Properties
C8H7ClO
Molar mass 154.59 g·mol−1
Appearance white to gray crystalline solid
Odor pungent and irritating
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)
insoluble
Vapor pressure 0.005 mmHg (20 °C)
Hazards
Main hazards Combustible
Toxic T
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 88 °C (190 °F; 361 K)
Lethal dose or concentration (LD, LC):
417 mg/m3 (rat, 15 min)
600 mg/m3 (mouse, 15 min)
465 mg/m3 (rabbit, 20 min)
490 mg/m3 (guinea pig, 30 min)
159 mg/m3 (human, 20 min)
850 mg/m3 (human, 10 min)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 0.3 mg/m3 (0.05 ppm)
REL (Recommended)
 TWA 0.3 mg/m3 (0.05 ppm)
IDLH (Immediate danger)
 15 mg/m3
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. It should not be confused with cyanide, another agent used in chemical warfare, which has the chemical structure CN−.

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:

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

Because of its significantly greater toxicity, 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 facial tissues (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.


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