Chemistry:Chloramine-T
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| Preferred IUPAC name
Sodium chloro(4-methylbenzene-1-sulfonyl)azanide | |
Other names
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| Properties | |
| C7H7ClNO2S·Na C7H7ClNO2S·Na·(3H2O) (hydrate) | |
| Molar mass | 227.64 g/mol 281.69 g/mol (trihydrate) |
| Appearance | White powder |
| Density | 1.4 g/cm3 |
| Melting point | Releases chlorine at 130 °C (266 °F; 403 K) Solid melts at 167–169 °C |
| >100 mg/mL (hydrate)[1] | |
| Pharmacology | |
| 1=ATC code }} | D08AX04 (WHO) QP53AB04 (WHO) |
| Hazards | |
| Main hazards | Corrosive |
| GHS pictograms |   
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| GHS Signal word | Danger |
| H302, H314, H334 | |
| P260, P261, P264, P270, P280, P285, P301+312, P301+330+331, P303+361+353, P304+340, P304+341, P305+351+338, P310, P321, P330, P342+311, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
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][3] 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 mild 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.
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]
Certifications
- EN 1276 Bactericidal
- EN 13713 Bactericidal
- EN 14675 Virucidal
- EN 14476 Virucidal Norovirus
- EN 1650 Fungicidal
- EN 13704 Sporicidal Clostridium difficile
References
- ↑ "Chloramine-T hydrate". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/sigma/c9887?lang=en.
- ↑ 2.0 2.1 2.2 Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo reagents". Chemical Reviews 78: 65–79. doi:10.1021/cr60311a005.
- ↑ 3.0 3.1 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): 101416. 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.
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". Archived from the original on 2009-12-25. https://web.archive.org/web/20091225181638/http://disifinusa.com/. Retrieved 2010-02-09.
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