|Preferred IUPAC name
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 soluble in water, miscible with alcohol and ether|
|Vapor pressure||34.9 kPa (20 °C)|
|GHS Signal word||Danger|
|P210, P233, P240, P241, P242, P243, P280, P303+361+353, P370+378, P403+235, P501|
|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).
|what is ?)(|
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.
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.
|Step 1||Step 2||Step 3|
|The acid protonates the alcohol, forming a good leaving group (water).||Water leaves the protonated t-BuOH, forming a relatively stable tertiary carbocation.||The chloride ion attacks the carbocation, forming t-BuCl.|
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.
tert-Butyl chloride is used to prepare the antioxidant tert-butylphenol and the fragrance neohexyl chloride.