N
‐Halamines are inorganic and organic compounds in which oxidative halogen is chemically bonded to nitrogen. They have both research and commercial importance, particularly in the areas of disinfection of water and stabilization of free halogen. The
N
‐halogen bond is formed by reaction of an amine, imine, amide, or imide with halogen, hypohalous acid, or hypochlorite. Only the chloro and bromo derivatives are of commercial importance. The physical and chemical properties, preparation, manufacture, uses, safety and handling, toxicity, and economic aspects of chloramines and bromamines are discussed. The chemistry of chloramines and bromamines is diversified not only because nitrogen and halogen act as reaction sites, but because of the different modes by which these functionalities react. Research activity on synthetic applications of chloramines and bromamines continues to be high.
In aqueous solution, the chloramines and bromamines generally undergo hydrolysis to varying degrees forming hypochlorous and hypobromous acids. Thus generally these
N
‐halamines can be considered as halogen release agents, and many, eg, chloroisocyanurates, find use in bleaching, disinfecting, and sanitizing applications. Others, such as halogen derivatives of ammonia, are important because they are industrial process intermediates (monochloramine) or of significance in water treatment (mono‐, di‐, and trichloramine). The most recent work has concerned covalent attachment of
N
‐halamine moieties to insoluble polymers so as to create biocidal materials with excellent potential for commercial utilization.
