tert-Butyl chloride is the organochloride with the formula (CH3)3CCl. 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.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||92.57 g/mol|
|Melting point||−26 °C (−15 °F; 247 K)|
|Boiling point||51 °C (124 °F; 324 K)|
|Sparingly sol in water, miscible with alcohol and ether|
|Vapor pressure||34.9 kPa (20 °C)|
|R-phrases (outdated)||R12, R36/37/38|
|S-phrases (outdated)||S7, S9, S16, S29, S33|
|NFPA 704 (fire diamond)|
|Flash point|| −9 °C (16 °F; 264 K) (open cup)|
−23 °C (closed cup)
|540 °C (1,004 °F; 813 K)|
Related alkyl halides
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 SN1 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 SN1 mechanism to be followed, whereas a primary alcohol would follow an SN2 mechanism.