Chemistry: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.[1] It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles.[2] 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.[1]
It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced in situ from sodium hydroxide and chlorine (Cl2):[1]
450px
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.[3] 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 (bis(2-chloroethyl) sulfide) to yield a harmless crystalline sulfimide.[4]
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.[5]
Disinfectant
Chloramine-T has a long history as a hospital disinfectant. It is effective against e.g. hepatitis and HI viruses.[6] Unlike the more common sodium hypochlorite, chloramine-T is mildly basic, almost odorless and is not a bleaching agent.[7]
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.[8] Chloramine-T has been observed to cause occupational asthma and flu-like symptoms.[6][9]
Certifications
- EN 1276 Bactericidal
- EN 13713 Bactericidal
- EN 14675 Virucidal
- EN 14476 Virucidal Norovirus
- EN 1650 Fungicidal
- EN 13704 Sporicidal Clostridioides difficile
References
- ↑ 1.0 1.1 1.2 Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo reagents". Chemical Reviews 78: 65–79. doi:10.1021/cr60311a005.
- ↑ 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" (in en). Journal of Saudi Chemical Society 26 (2). doi:10.1016/j.jscs.2021.101416. ISSN 1319-6103.
- ↑ 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.
- ↑ Ura, Yasukazu; Sakata, Gozyo (2007). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553.
- ↑ Rösch, F.. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. 4. Dordrecht, Boston, London: Kluwer Academic Publishers.
- ↑ 6.0 6.1 "Kloramiini-T-jauheesta ammattiastmaa ja nuhaa välinehuoltotyössä" (in Fi). February 23, 1995. https://www.duodecimlehti.fi/duo50224.
- ↑ "Sactiv Kloramiini 1l" (in fi). https://www.sillasiisti.fi/sactiv-kloramiini-1l.
- ↑ https://www.carlroth.com/medias/SDB-0271-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMDc2NDF8YXBwbGljYXRpb24vcGRmfGgwYi9oZjEvOTE0MzI0MzgwMDYwNi9TREJfMDI3MV9HQl9FTi5wZGZ8NzE3ODFiZjc3YjFlZTk1MWExMjUxOWU2YzJhOWEyZGY5ZDIxMzJjYTQ2NzU2MjI0MDBjMzVjZDMwMWJlODkyMQ [bare URL]
- ↑ https://www.ttl.fi/file-download/download/public/6517 [bare URL]
External links
- M. Shetty, T. B. Gowda (2004). "A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium". Zeitschrift für Naturforschung 59: 63–72. doi:10.1515/znb-2004-0110.
- Chemicalland21.com: Chloramine T (Tosylchloramide sodium)
- InChem.org: Chloramine T
- "Disifin USA". http://www.disifinusa.com.
 |  |
