Chloramine-T

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.
Reactions.
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 C6H5SO2NCl(H) is 9.5.
It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced "in situ" from sodium hydroxide and chlorine (Cl2):
Uses.
Reagent in amidohydroxylation.
The Sharpless oxyamination converts an alkene to a vicinal amino alcohol. A common source of the amido component of this reaction is chloramine-T. Vicinal amino-alcohols are important products in organic synthesis and recurring pharmacophores in drug discovery.
Oxidant.
Chloramine-T is a strong oxidant. It oxidizes hydrogen sulfide to sulfur and mustard gas to yield a harmless crystalline sulfimide.
It converts iodide to iodine monochloride (ICl). ICl rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid tyrosine. Thus, chloramine-T is used to incorporate iodine into peptides and proteins. Chloramine-T together with iodogen or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes.