tert-Butyl Hypochlorite
Title: tert-Butyl Hypochlorite
CAS Registry Number: 507-40-4
CAS Name: Hypochlorous acid 1,1-dimethylethyl ester
Additional Names: t-butyl hypochlorite
Molecular Formula: C4H9ClO
Molecular Weight: 108.57
Percent Composition: C 44.25%, H 8.36%, Cl 32.65%, O 14.74%
Line Formula: (CH3)3COCl
Literature 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.).
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. 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.
Boiling point: bp 77-78°
Index of refraction: nD20 1.403
Density: d2020 0.910; d418 0.9583
Use: Dehydration of alcohols; N- and C-chlorinations.

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