Chloramine-T is the organic compound with the formula CH3C6H4SO2NClNa. Both the anhydrous salt and its trihydrate are known. Both are white powders. Chloramine-T is used as a reagent in organic synthesis.[2] It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles.[3] It's inexpensive, has low toxicity and acts as a oxidizing agent. In addition, it also acts as a source of nitrogen anions and electrophilic cations. It may undergo degradation on long term exposure to atmosphere such that care must be taken during its storage.
Chloramine-T contains active (
electrophilic)
chlorine. Its reactivity is similar to that of
sodium hypochlorite. Aqueous solutions of chloramine-T are slightly basic (
pH typically 8.5). The
pKa of the closely related
N-chlorophenylsulfonamide C
6H
5SO
2NClH is 9.5.
[2]
It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced
in situ from
sodium hydroxide and chlorine (Cl
2):
[2]
