Thus, benzyl chloride is a lachrymator and has been used in chemical warfare. In contact with mucous membranes, hydrolysis produces hydrochloric acid. 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.
It is preferable over benzyl bromide for the preparation of this reagent, since the reaction of the bromide with magnesium tends to form the Wurtz coupling product 1,2-diphenylethane.īenzyl chloride is an alkylating agent. In organic synthesis, benzyl chloride is used to introduce the benzyl protecting group in reaction with alcohols, yielding the corresponding benzyl ether, carboxylic acids, and benzyl ester.īenzoic acid (C 6H 5COOH) can be prepared by oxidation of benzyl chloride in the presence of alkaline KMnO 4:Ĭ 6H 5CH 2Cl + 2 KOH + 2 → C 6H 5COOK + KCl + H 2Oīenzyl 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.īenzyl chloride also reacts readily with metallic magnesium to produce a Grignard reagent. Benzyl chloride reacts with aqueous sodium hydroxide to give dibenzyl ether. īenzyl ethers are often derived from benzyl chloride. Quaternary ammonium salts, used as surfactants, are readily formed by alkylation of tertiary amines with benzyl chloride. Phenylacetic acid, a precursor to pharmaceuticals, is produced from benzyl cyanide, which in turn is generated by treatment of benzyl chloride with sodium cyanide. Industrially, benzyl chloride is the precursor to benzyl esters, which are used as plasticizers, flavorants, and perfumes.
Benzyl chloride was first prepared from treatment of benzyl alcohol with hydrochloric acid. Other methods of production exist, such as the Blanc chloromethylation of benzene. Side products of the reaction include benzal chloride and benzotrichloride.
#CHROMIUM CHLORIDE USES FREE#
The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. In this way, approximately 100,000 tonnes are produced annually. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.īenzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: C 6H 5CH 3 + Cl 2 → C 6H 5CH 2Cl + HCl Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C 6H 5CH 2Cl.
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