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Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds.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 widely used members of the halamines.

Inorganic chloramines
Inorganic chloramines comprise three compounds: monochloramine (NH2Cl), dichloramine (NHCl2), and nitrogen trichloride (NCl3). Monochloramine is of broad significance as a disinfectant for water.

Organic chloramines


Organic chloramines feature the NCl functional group attached to an organic substituent. Examples include N-chloromorpholine (ClN(CH2CH2)2O), N-chloropiperidine, and N-chloroquinuclidinium chloride.

Chloramines are commonly produced by the action of sodium hypochlorite on secondary amines:
 * R2NH +  NaOCl  →  R2NCl  +  NaOH

Tert-butyl hypochlorite can be used instead of bleach:
 * R2NH +  t-BuOCl  →  R2NCl  +  t-BuOH

Swimming pools
Chloramines are formed by reaction of chlorine used to disinfect swimming pools with ammonia and urea introduced into the pools by human perspiration, saliva, mucus, urine, and other biologic substances, and by insects and other pests. Chloramines, especially trichloramine, are responsible for most of the "chlorine smell" of pools, as well as for skin, eye, and respiratory irritation.