1571. tert-Butyl Hypochlorite

Nomenclature

CAS number: 507-40-4
Hypochlorous acid 1,1-dimethylethyl ester; t-butyl hypochlorite.
C4H9ClO; mol wt 108.57.
C 44.25%, H 8.36%, Cl 32.65%, O 14.74%.

Description and references

Prepd by adding aq tert-butyl alcohol to a cooled aq soln of NaOH and passing chlorine into the mixture: Teeter, Bell, Org. Synth. 32, 20 (1952). By adding CO2 to neutral aq tert-butyl alcohol and NaOCl satd with NaCl: Katz, US 2694722 (1954 to Bjorksten Res. Labs.).

Chemical structure

Properties

Pale yellow liquid, irritating odor. d2020 0.910; d418 0.9583. bp 77-78°. nD20 1.403. Hydrolyzes in presence of aq alkali but not aq acid. Dec upon exposure to bright light to methyl chloride and acetone with considerable evolution of heat. Spontaneously combustible; corrosive. Should be stored in an inert atmosphere in a dark, refrigerated place. Violent reaction occurs if exposed to rubber, strong light or overheating. Has far greater stability than the corresponding n-butyl and sec-butyl hypochlorites.

Use

Dehydration of alcohols; N- and C-chlorinations.