''tert''-Butyl hypochlorite is the
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula (CH
3)
3COCl. A yellow liquid, it is a rare example of an organic
hypochlorite
In chemistry, hypochlorite, or chloroxide is an oxyanion with the chemical formula ClO−. It combines with a number of cations to form hypochlorite salts. Common examples include sodium hypochlorite (household bleach) and calcium 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
Sodium hypochlorite is an alkaline inorganic chemical compound with the formula (also written as NaClO). It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of ...
(bleach).
Synthesis and reactions
It is produced by chlorination of
''tert''-butyl alcohol in the presence of base:
:
''tert''-Butyl hypochlorite is useful in the preparation of organic
chloramines
Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds. Two classes of compounds are considered: inorganic chloramines and organic chloramines. Chloramines are the most wi ...
such as
chloramine-T:
:R
2NH + ''t''-BuOCl → R
2NCl + ''t''-BuOH
References
{{DEFAULTSORT:Butyl hypochlorite, tert-
Hypochlorite esters
Tert-Butyl esters