tertButylchlorid

tert-Butyl chloride, also known as 2-methylpropan-2-yl chloride, is an organochlorine compound with the formula C4H9Cl. It is a colorless, volatile liquid at room temperature and is classified as a tertiary alkyl chloride. The chlorine atom is attached to a quaternary carbon center in the tert-butyl group (CH3)3C–Cl.

Preparation and occurrence: It is typically prepared by converting tert-butanol to the chloride, for example by reaction with hydrogen chloride or with thionyl chloride (SOCl2). It can also be produced by chlorination of isobutane, which yields a mixture of chlorinated products including tert-butyl chloride.

Reactions: As a tertiary alkyl halide, it readily undergoes nucleophilic substitution via an SN1 mechanism, forming a variety of tert-butyl derivatives when treated with nucleophiles such as water, alcohols, amines, or carboxylates. Hydrolysis yields tert-butanol, and elimination under suitable conditions gives isobutene (2-methylpropene).

Uses: It is used as an alkylating agent to introduce bulky tert-butyl groups in organic synthesis. It serves as a starting material for the preparation of tert-butyl esters and tert-butyl ethers and is employed in routes that install the tert-butyl moiety in pharmaceuticals, natural products, and polymers.

Safety and handling: tert-Butyl chloride is flammable and corrosive to skin and eyes. It reacts with water to release hydrogen chloride. It should be handled in a well-ventilated area or fume hood, with appropriate gloves and eye protection, and stored in a dry, tightly closed container away from moisture.