tert-Butyl chloride is the organochloride with the formula . It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds.
tert-Butyl chloride is produced by the reaction of tert-butyl alcohol with hydrogen chloride. In the laboratory, concentrated hydrochloric acid is used. The conversion entails a S<sub>N</sub>1 reaction as shown below.
The overall reaction, therefore, is:
Because tert-butanol is a tertiary alcohol, the relative stability of the tert-butyl carbocation in the step 2 allows the S<sub>N</sub>1 mechanism to be followed, whereas a primary alcohol would follow an S<sub>N</sub>2 mechanism.
When tert-butyl chloride is dissolved in water, it undergoes a hydrolysis to tert-butyl alcohol. When dissolved in alcohols, the corresponding t-butyl ethers are produced.
tert-Butyl chloride is used to prepare the antioxidant tert-butylphenol and the fragrance base .