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] 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.

Chloramine-T

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
CAS Number	127-65-1 Y 7080-50-4 (trihydrate) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:53782 N
ChEMBL	ChEMBL1697734 N
ChemSpider	2876055 Y 29119 (free acid) Y
ECHA InfoCard	100.004.414
EC Number	204-854-7
KEGG	D02445 Y
PubChem CID	3641960 31388 (free acid)
UNII	328AS34YM6 Y 4IU6VSV0EI (trihydrate) Y
CompTox Dashboard (EPA)	DTXSID6040321
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 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 g/L (hydrate)[1]
Pharmacology
ATC code	D08AX04 (WHO) QP53AB04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Corrosive
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314, H334
Precautionary statements	P260, P261, 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). N verify (what is YN ?) 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 pK_a 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.

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

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