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tert-Butyl chloride

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tert-Butyl chloride
Names
Preferred IUPAC name
2-Chloro-2-methylpropane
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 Edit this at Wikidata
EC Number
  • 208-066-4
RTECS number
  • TX5040000
UNII
UN number 1127
  • InChI=1S/C4H9Cl/c1-4(2,3)5/h1-3H3 checkY
    Key: NBRKLOOSMBRFMH-UHFFFAOYSA-N checkY
  • ClC(C)(C)C
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 soluble in water, miscible with alcohol and ether
Vapor pressure 34.9 kPa (20 °C)
Hazards
GHS labelling:
GHS02: Flammable
Danger
H225
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
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).
checkY verify (what is checkY☒N ?)

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]

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:

(CH3)3COH + HCl → (CH3)3CCl + H2O

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.

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.

Uses

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

See also

References

  1. ^ a b c 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
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