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This colourless liquid is a reactive organochlorine compound that is a widely used chemical building block. Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: In this way, approximately , tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. Other methods of production exist, such as the Blanc chloromethylation of benzene. Benzyl chloride was first prepared from treatment of benzyl alcohol with hydrochloric acid. Industrially, benzyl chloride is the precursor to benzyl esters which are used as plasticizers , flavorants, and perfumes. Phenylacetic acid , a precursor to pharmaceuticals, is produced from benzyl cyanide, which is generated by treatment of benzyl chloride with sodium cyanide. Quaternary ammonium salts , used as surfactants , are readily formed by alkylation of tertiary amines with benzyl chloride. In organic synthesis , benzyl chloride is used for the introduction of the benzyl protecting group in reaction with alcohols , yielding the corresponding benzyl ether, carboxylic acids , and benzyl ester. Benzyl chloride may be used in the synthesis of amphetamine-class drugs, and for this reason, sales of benzyl chloride are monitored as a List II drug precursor chemical by the US Drug Enforcement Administration. Benzyl chloride also reacts readily with metallic magnesium to produce a Grignard Reagent. Benzyl chloride is an alkylating agent. Indicative of its high reactivity relative to alkyl chlorides , benzyl chloride reacts with water in a hydrolysis reaction to form benzyl alcohol and hydrochloric acid. In contact with mucous membranes, hydrolysis produces hydrochloric acid. Thus, benzyl chloride is a lachrymator and has been used in chemical warfare. It is also very irritating to the skin. It is classified as an extremely hazardous substance in the United States as defined in Section of the U. From Wikipedia, the free encyclopedia. Not to be confused with benzoyl chloride. Interactive image Interactive image. Refractive index n D. LD 50 median dose. LC 50 median concentration. LC Lo lowest published. Retrieved October 29, Retrieved from ' https: Views Read Edit View history. In other projects Wikimedia Commons. This page was last edited on 8 September , at By using this site, you agree to the Terms of Use and Privacy Policy. Lethal dose or concentration LD , LC:. Wikimedia Commons has media related to Benzyl chloride.

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