Tert-Butyl hypochlorite explained

tert-Butyl hypochlorite is the organic compound with the formula (CH₃)₃COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It can be viewed as a lipophilic version of sodium hypochlorite (bleach).^[1]

Synthesis and reactions

It is produced by chlorination of tert-butyl alcohol in the presence of base:^{[2] [3]}

tert-Butyl hypochlorite is useful in the preparation of organic chloramines:^[4]

R₂NH + t-BuOCl → R₂NCl + t-BuOH

Notes and References

1. Book: 10.1002/047084289X.rb388.pub2. t-Butyl Hypochlorite. Encyclopedia of Reagents for Organic Synthesis. 2006. Simpkins. Nigel S.. Cha. Jin K.. 0471936235.
2. tert-Butyl Hypochlorite. H. M.. Teeter. E. W.. Bell. Org. Synth.. 1952. 32. 20. 10.15227/orgsyn.032.0020.
3. t-Butyl Hypochlorite. H. M.. Mintz. C.. Walling. Org. Synth.. 1969. 49. 9. 10.15227/orgsyn.049.0009.
4. Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-[1-(2-hydroxy-1,2-diphenylethyl)]carbamate. Eugenio. Herranz. K. Barry. Sharpless. Org. Synth.. 1983. 61. 93. 10.15227/orgsyn.061.0093.