C6H5CH2Cl

C6H5CH2Cl, commonly known as benzyl chloride, is an organochlorine compound and a member of the benzyl halides. Its structure features a benzene ring bearing a chloromethyl substituent (CH2Cl). The systematic IUPAC name is chloromethylbenzene, with benzyl chloride being the widely used common name. Its molecular formula is C7H7Cl and its molecular weight is about 126.5 g/mol.

Benzyl chloride is primarily produced for industrial use by chlorinating benzyl alcohol or by chlorinating toluene under suitable conditions, with process variations depending on scale and purity requirements. It is a colorless to pale yellow, oily liquid that is relatively insoluble in water but soluble in many organic solvents. It has a boiling point near 179°C and a density around 1.08–1.12 g/mL at room temperature. It is a reactive benzylic halide and undergoes nucleophilic substitution readily, accommodating both SN1 and SN2 pathways depending on the reaction conditions.

Applications of benzyl chloride include uses as an intermediate in organic synthesis. It is a common reagent for forming benzyl ethers and esters (protections and protecting-group chemistry), as well as for introducing the benzyl moiety in pharmaceuticals, dyes, fragrances, and other chemical products. It can also react with ammonia or amines to give benzylamines after appropriate workup.

Safety and handling: benzyl chloride is hazardous and should be handled in a well-ventilated fume hood with appropriate personal protective equipment. It is a lachrymator and can be irritant to skin and eyes; it reacts with water to form benzyl alcohol and hydrochloric acid. It should be stored away from heat, moisture, and oxidizers and disposed of as a hazardous chemical according to applicable regulations.