1782 Bromoacetone Bromoacetone is an organobromide compound. It is a lachrymatory agent and was used in World War I as a chemical weapon (called BA by British and B-Stoff by Germans) and later as a riot control agent. Today it is considered obsolete (due to its toxicity) and is no longer in use for riot control purposes, but is a useful reagent in organic synthesis. Bromoacetone is prepared by combining bromine and acetone with a catalytic acid such as sulfuric acid. Bromoacetone has been shown to be a by-product of drinking water treatment using chlorine dioxide and chloramines in water high in bromide concentrations. Bromoacetone is found in the essential oil of a seaweed species (Asparagopsis taxiformis) that grows in the ocean around the Hawaiian Islands. Bromoacetone is structurally similar to chloroacetone. Both chemicals are irritants however, data suggest that bromoacetone is more toxic than chloroacetone. As a chemical warfare or riot control agent, bromoacetone is/was considered to be a rapid acting casualty producing agent capable of causing casualties within minutes of dissemination. Eye exposure to as little as 1 mg can cause pain and irritation. Inhalation of as little as 2-5 mg can cause coughing, nose and throat irritation and congestion. Inhalation of higher concentrations may lead to severe sore throat, nasal congestion and serious discomfort. Skin contact with as little as 2-30 mg can produce irritation, itching, swelling and general discomfort. Skin exposure to 50-100mg may lead to blisters. 598-31-2 11715 C3H5BrO 135.952380 Colorless liquid, with a pungent odour. Commercial product is yellow-brown. -36.5°C 137°C Oral (L626) ; inhalation (L626) ; dermal (L626) Organobromide compounds such as bromoacetone are strong alkylating agents. Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. Bromoacetone is a metabolic byproduct of bromopropane. It can react with glutathione and generate conjugates that are subsequently secreted in the urine. Very effecitve lachrymator at 1.5 mg/m3. Lethal at 3.2 mg/m3 for 10 min. No indication of carcinogenicity (not listed by IARC). (L135) Bromoacetone is an industrial and laboratory chemical. Occupational exposure to bromoacetone may occur through inhalation and dermal contact with this compound at workplaces where bromoacetone is produced or used. A strong lachrymator. Inhalation, ingestion or skin contact with material may cause severe injury or death. Animal studies indicate that at very high concentrations it can cause kidney and liver damage. Bromoacetone causes ocular irritation in 30% of human subjects at 0.1 ppm and 100% of human subjects at 1.0 ppm. Bromoacetone is a strong lachrymator. Inhalation leads to a burning sensation, cough, sore throat, labored breathing. Skin exposure causes redness, pain. Eyes exposure causes watering of the eyes, redness, pain, blurred vision. Ingestion leads to abdominal pain, burning sensation in the throat and chest, cough, diarrhea, nausea, vomiting. EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. 2009-06-22T16:08:35Z 2014-12-24T20:24:37Z 51845 ACETONE C018235 Bromoacetone true CC(=O)CBr C3H5BrO InChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3 InChIKey=VQFAIAKCILWQPZ-UHFFFAOYSA-N 136.975 135.952377429 Exogenous Liquid CHEMBL1085947 11223