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. 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):



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.
 * [[Image:Sharpless Oxyamination Scheme.png|350px|The Sharpless oxyamination]]

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.

Certifications

 * EN 1276 Bactericidal
 * EN 13713 Bactericidal
 * EN 14675 Virucidal
 * EN 14476 Virucidal Norovirus
 * EN 1650 Fungicidal
 * EN 13704 Sporicidal Clostridium difficile