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.

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 incorporate iodine into peptides and proteins. Chloramine-T together with iodogen or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes