532-27-4

tan crystalline powder

Riot control agent.

Colorless liquid, odorless to fruity.

Strong irritant to eyes and tissue as gas or liquid. Skin and upper respiratory tract irritant. Questionable carcinogen.

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)

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.

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.

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.

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.

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.

Chloroacetophenone is contained in tear gases (lacrimators). This substance has an important irritative potential but can also be a sensitizer.

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 alcohol
water solution. Hydrogen sulfide is liberated and collected by an alkaline scrubber.

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).

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

Chemical/Physical. Releases toxic chloride fumes when heated to decomposition (Sax and Lewis, 1987).

Color Code—Blue: Health Hazard: Store in asecure poison location. Prior to working with this chemicalyou should be trained on its proper handling and storage.Store in tightly closed containers in a refrigerator or cool,well-ventilated area away from oxidizers, heat, water, andsteam. Metal containers involving the transfer of this chemical should be grounded and bonded. Drums must beequipped with self-closing valves, pressure vacuum bungs,and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers ofthis chemical. Sources of ignition, such as smoking andopen flames, are prohibited where this chemical is used,handled, or stored in a manner that could create a potentialfire or explosion hazard.

Crystallise it from MeOH [Tanner J Org Chem 52 2142 1987]. [Beilstein 7 IV 641.]

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.