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.[2]

Chloramine-T
Names
IUPAC name
N-Chloro 4-methylbenzenesulfonamide, sodium salt
Other names
  • N-Chloro para-toluenesulfonylamide
  • Sodium chloro[(4-methyl phenyl)sulfonyl]azanide
  • Sodium N-chloro-4-methylbenzenesulphonomite
  • Chloraseptin
  • Chlorazol
  • Clorina
  • Disifin
  • Halamid
  • Hydroclonazone
  • Trichlorol
  • Minachlor
  • Tosylchloramide Sodium
  • N-chloro tosylamide, sodium salt
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.414
EC Number
  • 204-854-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula
 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
Solubility in water
 >100 mg/mL (hydrate)[1]
Pharmacology
ATC code
 D08AX04 (WHO) QP53AB04 (WHO)
Hazards
Main hazards Corrosive
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H302, H314, H334
GHS precautionary statements
 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).
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Infobox references

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 C6H5SO2NCl(H) 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 amino alcohol. A common source of the amido component of this reaction is chloramine-T.[3] Vicinal amino-alcohols are important products in organic synthesis and recurring pharmacophores in drug discovery.

The Sharpless oxyamination

Oxidant

Chloramine-T is a strong oxidant. It oxidizes hydrogen sulfide to sulfur and mustard gas 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. Thus, chloramine-T is used incorporate iodine into peptides and proteins. Chloramine-T together with iodogen or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes.[5]

Certifications
  • EN 1276 Bactericidal
  • EN 13713 Bactericidal
  • EN 14675 Virucidal
  • EN 14476 Virucidal Norovirus
  • EN 1650 Fungicidal
  • EN 13704 Sporicidal Clostridium difficile

References
  1. "Chloramine-T hydrate". Sigma-Aldrich.
  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. Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1, 2002, 2733–2746. (doi:10.1039/b111276g)
  4. Ura, Yasukazu; Sakata, Gozyo (2007). "Chloroamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553.
  5. F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4. Dordrecht/Boston/London: Kluwer Academic Publishers.