Phenacyl chloride
Names | |
---|---|
Preferred IUPAC name
2-Chloro-1-phenylethan-1-one | |
Other names
2-Chloro-1-phenylethanone
α-Chloroacetophenone 2-Chloroacetophenone Chloromethyl phenyl ketone Phenyl chloromethyl ketone CN Weeping gas[1] Mace | |
Identifiers | |
3D model (
JSmol ) |
|
ChEMBL | |
ChemSpider | |
ECHA InfoCard
|
100.007.757 |
IUPHAR/BPS |
|
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C8H7ClO | |
Molar mass | 154.59 g·mol−1 |
Appearance | white to gray crystalline solid[2] |
Odor | pungent and irritating[2] |
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)[2] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
Combustible[2] |
GHS labelling:[4] | |
Danger | |
H300, H311+H331, H315, H318, H334, H335 | |
P280, P301+P310+P330, P302+P352+P312, P304+P340+P311, P305+P351+P338+P310 | |
NFPA 704 (fire diamond) | |
Flash point | 88 °C (190 °F; 361 K) |
Lethal dose or concentration (LD, LC): | |
LCLo (lowest published)
|
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)[3] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
|
TWA 0.3 mg/m3 (0.05 ppm)[2] |
REL (Recommended)
|
TWA 0.3 mg/m3 (0.05 ppm)[2] |
IDLH (Immediate danger) |
15 mg/m3[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Phenacyl chloride, also commonly known as chloroacetophenone, is a substituted
, another agent used in chemical warfare, which has the chemical structure CN−. Chloroacetophenone is thermally stable, and is the only tear agent that is distillable at ambient conditions.Preparation
Chloroacetophenone was first synthetized by Graebe in 1871 by passing chlorine into boiling acetophenone.[6]
Phenacyl chloride is readily available and was first prepared by
Riot control agent
It was investigated, but not used, during the
Because of its significantly greater toxicity,[9] 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 and is less toxic 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
Like CS gas, this compound irritates the
At high concentrations, CN may cause
References
- ^ Verma, K.S. Cengage Physical Chemistry Part 1 Archived 2021-05-06 at the Wayback Machine, Illustration 5.65
- ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0119". National Institute for Occupational Safety and Health (NIOSH).
- ^ "alpha-Chloroacetophenone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ GHS: GESTIS 037810
- ^ S2CID 45123933.
- ^ Graebe, C. (1871), Ueber eine neue Klasse von Alkoholen. Ber. Dtsch. Chem. Ges., 4: 34-35.
- .
- ^ Levin, N.; Hartung, W. H. (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses; Collected Volumes, vol. 3, p. 191.
- ^ S2CID 35150415.
- S2CID 21164652.
- ^ doi=10.1096/fj.08-117812
- ^ doi=10.1016/j.taap.2008.04.005
External links
- Media related to Phenacyl chloride at Wikimedia Commons