Chloramine-T

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.

Quick facts Names, Identifiers ...
Chloramine-T
Ball-and-stick model of the component ions of chloramine-T
Chloramine-T trihydrate
Names
Preferred IUPAC name
Sodium chloro(4-methylbenzene-1-sulfonyl)azanide
Other names
  • N-Chloro-para-toluenesulfonylamide
  • Sodium N-chloro-4-methylbenzenesulphonomite
  • Chloraseptin
  • Chlorazol
  • Clorina
  • Disifin
  • Halamid
  • Hydroclonazone
  • Trichlorol
  • Minachlor
  • Tosylchloramide Sodium
  • N-chlorotosylamide, sodium salt
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.414 Edit this at Wikidata
EC Number
  • 204-854-7
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 g/L (hydrate)[1]
Pharmacology
D08AX04 (WHO) QP53AB04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H302, H314, H334
P260, 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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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.

The Sharpless oxyamination

Oxidant

Chloramine-T is a strong oxidant. It oxidizes hydrogen sulfide to sulfur, and mustard gas (bis(2-chloroethyl) sulfide) 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. This makes it a useful reagent in combination with an iodide ion source for iodination of peptides and proteins. Chloramine-T together with iodogen (1,3,4,6-Tetrachloro-3a,6a-diphenyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione) or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes.[6]

Disinfectant

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]

Safety

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]

Certifications

References

External links

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