tert-Butyl chloride

*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
CAS Number	507-20-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL346997 ;
ChemSpider	10054 ;
ECHA InfoCard	100.007.334
EC Number	208-066-4;
PubChem CID	10486;
RTECS number	TX5040000;
UNII	JN2YO95TZ0 ;
UN number	1127
CompTox Dashboard (EPA)	DTXSID2023937 ;
	InChI InChI=1S/C4H9Cl/c1-4(2,3)5/h1-3H3 Key: NBRKLOOSMBRFMH-UHFFFAOYSA-N ;
	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 pictograms
GHS Signal word	Danger
GHS hazard statements	H225
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P280, P303+361+353, P370+378, P403+235, P501
NFPA 704 (fire diamond)	3 2 0
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).

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:

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

[Ullmann-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

[1]

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