Product Code Database
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.
It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced in situ from sodium hydroxide and chlorine (Cl2):
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. This makes it a useful reagent in combination with an iodide ion source for iodination of peptides and proteins. Chloramine-T together with iodogen (1,3,4,6-Tetrachloro-3a,6a-diphenyltetrahydroimidazo4,5-dimidazole-2,5(1H,3H)-dione) or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes.
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 in drug discovery.
Oxidant
Chloramine-T is a strong oxidant. It oxidizes hydrogen sulfide to sulfur, and mustard gas (bis(2-chloroethyl) sulfide) to yield a harmless crystalline sulfimide.
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
Chloramine-T has been observed to cause occupational asthma and flu-like symptoms.
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