Chloramine-T

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Chloramine-T
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
  • Sodium N-chloro-4-methylbenzenesulphonomite
  • Chloraseptin
  • Chlorazol
  • Clorina
  • Disifin
  • Halamid
  • Hydroclonazone
  • Trichlorol
  • Minachlor
  • Tosylchloramide Sodium
  • N-chloro tosylamide, sodium salt
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.414 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H8ClNO2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,1H3 ☒N
    Key: NXTVQNIVUKXOIL-UHFFFAOYSA-N ☒N
  • InChI=1/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1
    Key: VDQQXEISLMTGAB-UHFFFAOYAP
  • [Na+].O=S(=O)([N-]Cl)c1ccc(cc1)C
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
D08AX04 (WHO) QP53AB04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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]

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
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

References

  1. ^ "Chloramine-T hydrate". Sigma-Aldrich.
  2. ^ a b c 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. ISBN 978-3527306732.
  5. ^ F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 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.</ref>
  • Chemicalland21.com: Chloramine T (Tosylchloramide sodium)
  • InChem.org: Chloramine T
  • "Disifin USA". Archived from the original on 2009-12-25. Retrieved 2010-02-09.
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