tert-Butyl chloride

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.[1]

tert-Butyl chloride
Names
IUPAC name
2-chloro-2-methyl propane
Other names
1,1-dimethylethyl chloride
1-chloro-1,1-dimethylethane
chlorotrimethylmethane
trimethylchloromethane
t-butyl chloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.334
EC Number
  • 208-066-4
RTECS number
  • TX5040000
UN number 1127
Properties
C4H9Cl
Molar mass 92.57 g/mol
Appearance Colorless liquid
Density 0.851 g/ml
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)
Hazards
Flammable (F)
R-phrases (outdated) R12, R36/37/38
S-phrases (outdated) S7, S9, S16, S29, S33
NFPA 704 (fire diamond)
3
2
0
Flash point −9 °C (16 °F; 264 K) (open cup)
−23 °C (closed cup)
540 °C (1,004 °F; 813 K)
Related compounds
tert-Butyl bromide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reactions

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.

Synthesis

tert-Butyl chloride is produced by the reaction of tert-butyl alcohol with hydrogen chloride.[1] In the laboratory, concentrated hydrochloric acid, is used. The conversion entails a SN1 reaction as shown below.[2]

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.

Uses

tert-Butyl chloride is used to prepare the antioxidant tert-butylphenol and the fragrance neohexyl chloride.[1]

References

  1. M. Rossberg et al. "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2
  2. James F. Norris and Alanson W. Olmsted "tert-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. doi:10.15227/orgsyn.008.0050

See also

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