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Benzyl bromide, also known as alpha-bromotoluene, is an organic compound with the chemical formula C6H5CH2Br. It is a colorless liquid at room temperature and pressure, though it can decompose to form hydrogen bromide upon exposure to light or air. Benzyl bromide is a lachrymator, meaning it causes irritation to the eyes and is a potent tear gas.

This compound is primarily used as a benzylating agent in organic synthesis. It readily reacts with nucleophiles to introduce the benzyl group (C6H5CH2-) into molecules. This is useful for protecting functional groups, particularly alcohols and amines, during chemical reactions. The benzyl group can later be removed under various conditions, regenerating the original functional group. Benzyl bromide is also employed in the synthesis of perfumes, pharmaceuticals, and dyes.

Due to its irritating and toxic properties, benzyl bromide should be handled with extreme caution in a well-ventilated area or fume hood. Appropriate personal protective equipment, including gloves and eye protection, is essential. Storage should be in a cool, dark place away from incompatible materials.