Chloramine-T

N-chloro tosylamide sodium salt, sold as chloramine-T, is a N-chlorinated and N-deprotonated sulfonamide used as a biocide and a mild disinfectant. It is a white powder that gives unstable solutions with water.

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Chemistry

As a N-chloro compound, it contains active (electrophilic) chlorine and can be compared to the O-chlorinated sodium hypochlorite. Chloramine-T is nearly neutral (pH typically 8.5). In water, it breaks down to the disinfectant hypochlorite. It can be used as a source of electrophilic chlorine in organic synthesis.

The sulfur adjacent to the nitrogen can stabilize a nitrogen anion (R₂N^–), so that the N-chloro sulfonyamide moiety can be deprotonated at nitrogen even with only sodium hydroxide.

Use as a biocide

Chloramine-T is used for disinfection and as an algicide, bactericide, germicide, for parasite control, and for drinking water disinfection. The molecular structure of toluenesulfonylamide is similar to para-aminobenzoic acid, an intermediate in bacterial metabolism, which is disrupted by this sulfonamide (in the same way as by a sulfa drug). Therefore, chloramine-T is capable of inhibiting with bacterial growth with two mechanisms, with the phenylsulfonamide moiety and the electrophilic chlorine.