Tosylchloramide

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Tosylchloramide
Chloramine T.png
Ball-and-stick model of the component ions of chloramine-T
Names
IUPAC name
N-chloro 4-methylbenzenesulfonamide, sodium salt
Other names
N-chloro para-toluenesulfonylamide,
sodium chloro[(4-methyl phenyl)sulfonyl]azanide, chloramine-T
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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KEGG
UNII
Properties
C7H7ClNO2S·Na (3H2O)
Molar mass 227.64 g/mol in usual tri-hydrated form 282 Daltons.
Appearance white powder
Density 1.4 g/cm³
Melting point
Hazards
Main hazards Corrosive
R-phrases R22 R31 R34 R42
S-phrases (S1/2) S7 S22 S26 S36/37/39 S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Tosylchloramide or N-chloro tosylamide, sodium salt, sold as chloramine-T, is a N-chlorinated and N-deprotonated sulfonamide used as a biocide and a mild disinfectant. It is a white powder that gives unstable solutions with water. Trade names of chloramine-T products include Chloraseptin, Chlorazol, Clorina, Disifin, Halamid, Hydroclonazone, Trichlorol, Minachlor, and generic Chloramin T or Tosylchloramide Sodium, among others.

Uses

Iodination and radioiodination

Hypochlorite released from chloramine-T acts as an effective oxidizing agent for iodide to form 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 widely used for the incorporation of iodine to peptides and proteins. Chloramine-T together with iodogen or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes (123I, 125I or 131I).[1]

Biocide

Chloramine-T is available in tablet or powder form and has to be dissolved before use. It is sprayed on a surface and allowed to stand for at least 15 minutes before being wiped off or allowed to dry. It used in areas such as hospitals, laboratories, nursing homes, funeral homes, medical, dental and veterinary facilities, where control of pathogens is required, for disinfecting surfaces and soaking medical and dental equipment. The substance is also used for parasite control and for drinking water disinfection.

Chloramine-T is as an algicide, bactericide, virucide, fungicide (including spores), germicide. It is also effective against mycobacteria such as tuberculosis, foot-and-mouth disease and avian influenza. The molecular structure of toluenesulfonylamide is similar to para-aminobenzoic acid, an intermediate in bacterial metabolism, which is disrupted by this sulfonamide (in the same way as by a sulfa drug). Therefore, chloramine-T is capable of inhibiting with bacterial growth with two mechanisms, with the phenylsulfonamide moiety and the hypochlorite, which destroys the DNA structure via oxidation and thereby prevents microbes from reproducing and reforming.

Protective agent

Chloramine-T reacts readily with mustard gas to yield a harmless crystalline sulfimide; chloramine-T derivatives are being studied as protective agents against poison gas.[2]

Certifications

References

  1. F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4. Dordrecht/Boston/London: Kluwer Academic Publishers.
  2. Yasukazu Ura; Gozyo Sakata (2007), "Chloroamines", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5

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