Chemistry:Tert-Butyl chloride

From HandWiki
tert-Butyl chloride
Tert-butyl-chloride-2D-skeletal.png
Tert-butyl-chloride-3D-balls.png
Tert butyl chloride.jpg
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
EC Number
  • 208-066-4
RTECS number
  • TX5040000
UNII
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 soluble in water, miscible with alcohol and ether
Vapor pressure 34.9 kPa (20 °C)
Hazards
GHS pictograms GHS02: Flammable
GHS Signal word Danger
H225
P210, P233, P240, P241, P242, P243, P280, P303+361+353, P370+378, P403+235, P501
NFPA 704 (fire diamond)
Flammability code 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. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored 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
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).
☑Y verify (what is ☑Y☒N ?)
Infobox references
Tracking categories (test):

tert-Butyl chloride is the organochloride with the formula (CH
3)
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
1-HCl-protonates-tBuOH-2D-skeletal.png 250px 3-chloride-attacks-tBu-cation-2D-skeletal.png
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:

(CH
3)
3COH + HCl → (CH
3)
3CCl + H
2O

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. ↑ 1.0 1.1 1.2 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

External links



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Tert-Butyl_chloride&oldid=2605806"