tert-Butyl chloride

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tert-Butyl chloride - Wikipedia

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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

CAS Number

507-20-0^Y

3D model (JSmol)

Interactive image

ChEMBL

ChEMBL346997^Y

ChemSpider

10054^Y

ECHA InfoCard

100.007.334

EC Number

208-066-4

PubChem CID

10486

RTECS number

TX5040000

UNII

JN2YO95TZ0^Y

UN number

1127

CompTox Dashboard (EPA)

DTXSID2023937

InChI

InChI=1S/C4H9Cl/c1-4(2,3)5/h1-3H3^Y
Key: NBRKLOOSMBRFMH-UHFFFAOYSA-N^Y

SMILES

ClC(C)(C)C

Properties

Chemical formula

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)

Solubility in water

Sparingly soluble in water, miscible with alcohol and ether

Vapor pressure

34.9 kPa (20 °C)

Hazards

GHS labelling:

Pictograms

Signal word

Danger

Hazard statements

H225

Precautionary statements

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501

NFPA 704 (fire diamond)

Flash point

−9 °C (16 °F; 264 K) (open cup)
−23 °C (closed cup)

Autoignition
temperature

540 °C (1,004 °F; 813 K)

Related compounds

Related alkyl halides

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

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 S_N1 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 S_N1 mechanism to be followed, whereas a primary alcohol would follow an S_N2 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]

References

^ ^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
^ James F. Norris and Alanson W. Olmsted "tert-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. doi:10.15227/orgsyn.008.0050

External links

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Synthesis

Reactions

Uses

See also

References

External links