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2-Chloroacetophenone

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2-Chloroacetophenone Basic information
2-Chloroacetophenone Chemical Properties
  • Melting point:54-56 °C(lit.)
  • Boiling point:244-245 °C(lit.)
  • Density 1.324 g/mL at 25 °C(lit.)
  • vapor pressure 4 at 20 °C, 14 at 30 °C (quoted, Verschueren, 1983)
  • refractive index 1.5438
  • Flash point:118°C
  • solubility Soluble in acetone (Weast, 1986). Freely soluble in alcohol, benzene, and ether (Windholz et al., 1983)
  • form Colorless crystals
  • Water Solubility insoluble. <0.1 g/100 mL at 19 ºC
  • Sensitive Moisture Sensitive
  • Merck 14,2115
  • BRN 507950
  • Exposure limitsNIOSH REL: TWA 0.3 mg/m3 (0.05 ppm), IDLH 15 mg/m3; OSHA PEL: TWA 0.05 ppm (0.3 mg/m3); ACGIH TLV: TWA 0.05 ppm (adopted).
  • Stability:May decompose upon exposure to air or water. Incompatible with bases, amines, alcohols.
  • InChIKeyIMACFCSSMIZSPP-UHFFFAOYSA-N
  • CAS DataBase Reference532-27-4(CAS DataBase Reference)
  • NIST Chemistry ReferenceEthanone, 2-chloro-1-phenyl-(532-27-4)
  • EPA Substance Registry System2-Chloroacetophenone (532-27-4)
Safety Information
MSDS
2-Chloroacetophenone Usage And Synthesis
  • DescriptionChloroacetophenone is contained in tear gases (lacrimators). This substance has an important irritative potential but can also be a sensitizer.
  • Chemical Propertiestan crystalline powder
  • Chemical Properties2-Chloroacetophenone (CN) is a combustible, colorless-to-gray solid. CN has a sharp, irritating odor, has been described as smelling like “apple blossoms.” It may be dissolved in a solvent
  • Physical propertiesColorless to gray crystalline solid with a sharp, penetrating, irritating odor. The low odor and high odor threshold concentrations were 102 and 150 μg/m3, respectively (Ruth, 1986).
  • UsesRiot control agent.
  • UsesChemical warfare agent (CN); principal constituent in riot control agent Mace; in tear gas formulations for personal protection devices
  • UsesCN is used as a nonlethal or less-than-lethal chemical in riot control situations to distract, deter, incapacitate, disorient, or disable disorderly people; to clear facilities or areas; to deny areas; or for hostage rescue. It can also be used in peacekeeping operations. It is also used in military training as a confidence builder for the protective mask.
  • DefinitionA strong lachrymator.
  • Synthesis Reference(s)The Journal of Organic Chemistry, 49, p. 2032, 1984 DOI: 10.1021/jo00185a046
    Tetrahedron, 51, p. 703, 1995 DOI: 10.1016/0040-4020(94)00989-8
    Tetrahedron Letters, 13, p. 4661, 1972
  • General DescriptionColorless liquid, odorless to fruity.
  • HazardStrong irritant to eyes and tissue as gas or liquid. Skin and upper respiratory tract irritant. Questionable carcinogen.
  • Health HazardMedian lethal dose (mg-min/m3): 11000 (estimated). Median incapacitating dose: 80. Eye/skin toxicity: Temporarily severe eye irritation; mild skin irritation. Rate of action: Instantaneous. Physiological action: Powerfully lacrimatory. Detoxification rate: Rapid. (ANSER)
  • Fire HazardCombustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
  • Contact allergensw-Chloroacetophenone is contained in tear gases (lacrimators). This substance has important irritative potential, but can also be a sensitizer.
  • Safety ProfileA human poison by inhalation. An experimental poison by ingestion, inhalation, intraperitoneal, and intravenous routes. Human systemic effects by inhalation: lachrymation, conjunctiva irritation, and unspecified eye effects, cough, and dyspnea. A severe eye and moderate skin irritant. Questionable carcinogen with experimental neoplastigenic data by skin contact. A riot control agent. When heated to decomposition it emits toxic fumes of Cl-. See also KETONES.
  • Potential ExposureChloroacetophenone is used as a chemical warfare agent (Agent CN) and as a principal ingredient in the riot control agent Mace. It is also used as a pharmaceutical intermediate. The United States considers agent CN and its mixtures with various chemicals to be obsolete for military deployment.
  • Environmental FateChemical/Physical. Releases toxic chloride fumes when heated to decomposition (Sax and Lewis, 1987).
  • ShippingUN1697 Chloroacetophenone, solid, (CN), Hazard Class: 6.1; Labels: 6.1-Poison Inhalation. UN3416 Chloroacetophenone, liquid, (CN), Hazard Class: 6.1;Labels: 6.1-Poisonous materials. Hazard. Military driver shall be given full and complete information regarding shipment and conditions in case of emergency. AR 50-6 deals specifically with the shipment of chemical agents. Shipments of agent will be escorted in accordance with AR 740-32.
  • Purification MethodsCrystallise it from MeOH [Tanner J Org Chem 52 2142 1987]. [Beilstein 7 IV 641.]
  • Toxicity evaluationCN has a half-life under aerobic conditions of 672 h and can be biodegraded in most moist, nutrient-rich soil.
    Biodegradation in water is similar to degradation in soil. Howard et al. (1991) reports the same 672 h half-life for CN in aerobic surface water. This half-life is extended up to 2688 h for anaerobic aqueous degradation.
    Volatile losses of CN from surface waters can be another significant process for CN disappearance in water. For instance, Olajos and Stopford (2004) calculated that CN contamination in a river would have a half-life of approximately 14 days, while CN contamination in a lake would have a half-life of approximately 110 days.
  • IncompatibilitiesKeep away from water, steam, strong oxidizers. CN reacts with water, forming hydrochloric acid. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. CN reacts slowly with metals, causing mild corrosion and may evolve flammable hydrogen gas.
  • Waste DisposalTear gas-containing waste is dissolved in an organic solvent and sprayed into an incinerator equipped with an afterburner and alkaline scrubber utilizing reaction with sodium sulfide in an alcoholwater solution. Hydrogen sulfide is liberated and collected by an alkaline scrubber.
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