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 chlorine. Its reactivity is similar to that of sodium hypochlorite. Aqueous solutions of chloramine-T are slightly basic. The pKa of the closely related N-chlorophenylsulfonamide C6H5SO2NCl 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 :

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 rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid tyrosine. Thus, chloramine-T is used incorporate iodine into peptides and proteins. Chloramine-T together with iodogen or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes.

Certifications