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Chloramine-T

C7H7ClNO2S·Na·(3H2O) (hydrate) 281.69 g/mol (trihydrate) Solid melts at 167–169 °C

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. :[[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 (bis(2-chloroethyl) sulfide) 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. 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-diphenyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione) 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

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

References

"Chloramine-T hydrate". [[Sigma-Aldrich]].
(1978). "Chloramine T and Related ''N''-halogeno-''N''-metallo reagents". Chemical Reviews.
(2022-03-01). "Chloramine-T (N-chloro-p-toluenesulfonamide sodium salt), a versatile reagent in organic synthesis and analytical chemistry: An up to date review". Journal of Saudi Chemical Society.
(2002). "The Sharpless asymmetric aminohydroxylation". J. Chem. Soc., Perkin Trans. 1.
(2007). "Chloroamines".
Rösch, F.. "Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences". Kluwer Academic Publishers.
(February 23, 1995). "Kloramiini-T-jauheesta ammattiastmaa ja nuhaa välinehuoltotyössä".
"Sactiv Kloramiini 1l".
(August 2025{{Dead link). (December 2025)
https://www.ttl.fi/file-download/download/public/6517 {{Bare URL inline. (August 2025)

Info: Wikipedia Source

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antiseptics pesticides sulfonamides chlorides organic-sodium-salts p-tosyl-compounds nitrogen–halogen-compounds sulfur–nitrogen-compounds

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