| | 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 | | Fp | 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 limits | NIOSH 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. | | InChIKey | IMACFCSSMIZSPP-UHFFFAOYSA-N | | LogP | 1.724 (est) | | CAS DataBase Reference | 532-27-4(CAS DataBase Reference) | | NIST Chemistry Reference | Ethanone, 2-chloro-1-phenyl-(532-27-4) | | EPA Substance Registry System | 2-Chloroacetophenone (532-27-4) |
| | 2-Chloroacetophenone Usage And Synthesis |
| Description | Chloroacetophenone is contained in tear gases (lacrimators).
This substance has an important irritative
potential but can also be a sensitizer. | | Chemical Properties | 2-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 properties | Colorless 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). | | Uses | Riot control agent. | | Uses | Chemical warfare agent (CN); principal
constituent in riot control agent Mace; in
tear gas formulations for personal protection
devices | | Uses | 2-Chloroacetophenone 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. | | Definition | A 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 Description | 2-chloroacetophenone appears as a white crystalline solid. Denser than water and insoluble in water. Hence sinks in water. A lachrymator: vapors are very irritating to the eyes. Has a floral odor. Used as a riot control agent. | | Hazard | The main uses for 2-chloroacetophenone are in tear gas and in chemical Mace. It is a potent eye, throat, and skin irritant. Acute (short-term) inhalation exposure of humans causes burning of the eyes with lacrimation, some degree of blurred vision, possible corneal damage, irritation and burning of the nose, throat, and skin, and burning in the chest with dyspnea. Acute dermal exposure is irritating and can result in first, second, and third degree chemical burns in humans. Squamous hyperplasia of the nasal respiratory epithelium was reported in rats chronically exposed (long-term) via inhalation. EPA has not classified 2-chloroacetophenone with respect to potential carcinogenicity. | | Health Hazard | Median 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 Hazard | Combustible 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 allergens | w-Chloroacetophenone is contained in tear gases (lacrimators).
This substance has important irritative
potential, but can also be a sensitizer. | | Safety Profile | A 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 Exposure | Chloroacetophenone 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 fate | Chemical/Physical. Releases toxic chloride fumes when heated to decomposition (Sax and
Lewis, 1987). | | Shipping | UN1697 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 Methods | Crystallise it from MeOH [Tanner J Org Chem 52 2142 1987]. [Beilstein 7 IV 641.] | | Toxicity evaluation | CN 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. | | Incompatibilities | Keep 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 Disposal | Tear 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. |
| | 2-Chloroacetophenone Preparation Products And Raw materials |
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