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. It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles. 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.

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 C6H5SO2NClH 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 aminoalcohol. A common source of the amido component of this reaction is chloramine-T. Vicinal aminoalcohols 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.

Disinfectant

Chloramine-T has a long history as a hospital disinfectant. It is effective against e.g. hepatitis and HI viruses. Unlike the more common sodium hypochlorite, chloramine-T is mildly basic, almost odorless and is not a bleaching agent.

Safety

Chloramine-T is harmful if swallowed. It is corrosive on skin, eyes or mucous membranes. It releases toxic chlorine gas upon reaction with acids. It is water-soluble and thus can be released to the environment dissolved in water. It is a known sensitizer. Chloramine-T has been observed to cause occupational asthma and flu-like symptoms.

Certifications