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.[2] It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles.[3] 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.[2]

It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced in situ from sodium hydroxide and chlorine (Cl2):[2]

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.[4] Vicinal aminoalcohols are important products in organic synthesis and recurring pharmacophores in drug discovery.

The Sharpless oxyamination

Oxidant

Chloramine-T is a strong oxidant.[contradictory] It oxidizes hydrogen sulfide to sulfur and mustard gas to yield a harmless crystalline sulfimide.[5]

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.[6]

Disinfectant

Chloramine-T has a long history as a hospital disinfectant. It is effective against e.g. hepatitis and HI viruses.[7] Unlike the more common sodium hypochlorite, chloramine-T is mildly basic, almost odorless and is not a bleaching agent.[8]

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.[9] Chloramine-T has been observed to cause occupational asthma and flu-like symptoms.[7][10]

Certifications

References

  1. ^ "Chloramine-T hydrate". Sigma-Aldrich.
  2. ^ a b c Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo reagents". Chemical Reviews. 78: 65–79. doi:10.1021/cr60311a005.
  3. ^ Nayak, Yogeesha N.; Gaonkar, Santosh L.; Saleh, Ebraheem Abdu Musad; Dawsari, Abdullah Mohammed A. L.; Harshitha; Husain, Kakul; Hassan, Ismail (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. 26 (2): 101416. doi:10.1016/j.jscs.2021.101416. ISSN 1319-6103.
  4. ^ Bodkin, J. A.; McLeod, M. D. (2002). "The Sharpless asymmetric aminohydroxylation". J. Chem. Soc., Perkin Trans. 1. 2002 (24): 2733–2746. doi:10.1039/b111276g.
  5. ^ Ura, Yasukazu; Sakata, Gozyo (2007). "Chloroamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553. ISBN 978-3-527-30673-2.
  6. ^ Rösch, F. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Vol. 4. Dordrecht, Boston, London: Kluwer Academic Publishers.
  7. ^ a b https://www.duodecimlehti.fi/duo50224
  8. ^ "Sactiv Kloramiini 1l". www.sillasiisti.fi (in Finnish). Retrieved 2024-10-25.
  9. ^ https://www.carlroth.com/medias/SDB-0271-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMDc2NDF8YXBwbGljYXRpb24vcGRmfGgwYi9oZjEvOTE0MzI0MzgwMDYwNi9TREJfMDI3MV9HQl9FTi5wZGZ8NzE3ODFiZjc3YjFlZTk1MWExMjUxOWU2YzJhOWEyZGY5ZDIxMzJjYTQ2NzU2MjI0MDBjMzVjZDMwMWJlODkyMQ
  10. ^ https://www.ttl.fi/file-download/download/public/6517
Allikas: https://en.wikipedia.org/wiki/Chloramine-T
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