Chemical compound From Wikipedia, the free encyclopedia
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.
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| Preferred IUPAC name
Sodium chloro(4-methylbenzene-1-sulfonyl)azanide | |
Other names
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3D model (JSmol) |
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| ECHA InfoCard | 100.004.414 |
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CompTox Dashboard (EPA) |
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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 g/L (hydrate)[1] | |
| Pharmacology | |
| D08AX04 (WHO) QP53AB04 (WHO) | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Corrosive |
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| Danger | |
| H302, H314, H334 | |
| P260, P261, P264, P270, P280, P285, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P321, P330, P342+P311, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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.
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]
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]
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]
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