Phenacyl chloride

Phenacyl chloride
Skeletal formula
Ball-and-stick model
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 Edit this at Wikidata
UNII
  • InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
  • c1ccc(cc1)C(=O)CCl
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]
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
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)[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).
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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.

  1. ^ Verma, K.S. Cengage Physical Chemistry Part 1 Archived 2021-05-06 at the Wayback Machine, Illustration 5.65
  2. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0119". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "alpha-Chloroacetophenone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ GHS: GESTIS 037810
  5. ^ 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.