Chloramine-T

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, sodium N-chloro-4-methylbenzenesulphonomite
Identifiers
CAS Number	127-65-1^Y 7080-50-4 (trihydrate)^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:53782^N
ChEMBL	ChEMBL1697734^N
ChemSpider	2876055^Y 29119 (free acid)^Y
ECHA InfoCard	100.004.414
KEGG	D02445^Y
PubChem	10198484 31388 (free acid)
UNII	328AS34YM6^N 4IU6VSV0EI (trihydrate)^N
InChI 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
SMILES [Na+].O=S(=O)([N-]Cl)c1ccc(cc1)C
Properties
Chemical formula	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	releases chlorine at 130 °C (266 °F; 403 K) solid melts at 167–169 °C
Solubility in water	15% in water (25 °C) 7.5% in rectified spirit (20 °C) insoluble in benzene and ethers
Pharmacology
ATC code	D08AX04 (WHO) QP53AB04 (WHO)
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).
N (what is ^YN ?)
Infobox references

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.

As an N-chloro compound, it contains active (electrophilic) chlorine and can be compared to the O-chlorinated sodium hypochlorite. Chloramine-T is slightly basic (pH typically 8.5). In water, it breaks down to the disinfectant hypochlorite. It can be used as a source of electrophilic chlorine in organic synthesis.

The anionic sulfonamide is stabilized by delocalization of the nitrogen lone pair across the SO₂ group, facilitating deprotonation of the parent amine by bases such as hydroxide. It is readily biodegradable by use of ultraviolet (UV) light.

Chloramine-T is prepared from p-toluenesulfonamide and sodium hypochlorite, with the latter being produced in situ from sodium hydroxide and chlorine (Cl₂).

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Wikipedia