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Phenacyl chloride
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| 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)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.757 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
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Combustible[2] |
| GHS labelling:[4] | |
  
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| 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)
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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)
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TWA 0.3 mg/m3 (0.05 ppm)[2] |
REL (Recommended)
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TWA 0.3 mg/m3 (0.05 ppm)[2] |
IDLH (Immediate danger)
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15 mg/m3[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenacyl chloride, also commonly known as chloroacetophenone, 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.[5] It should not be confused with cyanide, 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.
- ^ 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
- ^ Treudler, R.; Tebbe, B.; Blume-Peytavi, U.; Krasagakis, K.; Orfanos, C. E. (1999). "Occupational contact dermatitis due to 2-chloracetophenone tear gas". British Journal of Dermatology. 140 (3): 531–534. doi:10.1046/j.1365-2133.1999.02724.x. PMID 10233281. S2CID 45123933.
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