Chloramine-T

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 ; 7080-50-4 (trihydrate) ;
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:53782 ;
ChEMBL	ChEMBL1697734 ;
ChemSpider	2876055 ; 29119 (free acid) ;
ECHA InfoCard	100.004.414
EC Number	204-854-7;
KEGG	D02445 ;
PubChem CID	3641960 ; 31388 (free acid);
UNII	328AS34YM6 ; 4IU6VSV0EI (trihydrate) ;
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 Key: NXTVQNIVUKXOIL-UHFFFAOYSA-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 at130 °C (266 °F; 403 K) ; Solid melts at 167–169 °C
Solubility in water	>100 g/L (hydrate)
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). verify (what is ?) Infobox references

Last updated May 23, 2025

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.

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

References

↑ "Chloramine-T hydrate". Sigma-Aldrich.
1 2 3 Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo reagents". Chemical Reviews. 78: 65–79. doi:10.1021/cr60311a005.
↑ Nayak, Yogeesha N.; Gaonkar, Santosh L.; Saleh, Ebraheem Abdu Musad; Dawsari, Abdullah Mohammed A. L.; Harshitha; Husain, Kakul; Hassan, Ismail (2022-03-01). "Chloramine-T (N-chloro-p-toluenesulfonamide sodium salt), a versatile reagent in organic synthesis and analytical chemistry: An up to date review". Journal of Saudi Chemical Society. 26 (2): 101416. doi: 10.1016/j.jscs.2021.101416 . ISSN 1319-6103.
↑ Bodkin, J. A.; McLeod, M. D. (2002). "The Sharpless asymmetric aminohydroxylation". J. Chem. Soc., Perkin Trans. 1. 2002 (24): 2733–2746. doi:10.1039/b111276g.
↑ Ura, Yasukazu; Sakata, Gozyo (2007). "Chloroamines". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553. ISBN 978-3-527-30673-2.
↑ Rösch, F. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Vol. 4. Dordrecht, Boston, London: Kluwer Academic Publishers.
1 2 https://www.duodecimlehti.fi/duo50224
↑ "Sactiv Kloramiini 1l". www.sillasiisti.fi (in Finnish). Retrieved 2024-10-25.
↑ https://www.carlroth.com/medias/SDB-0271-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMDc2NDF8YXBwbGljYXRpb24vcGRmfGgwYi9oZjEvOTE0MzI0MzgwMDYwNi9TREJfMDI3MV9HQl9FTi5wZGZ8NzE3ODFiZjc3YjFlZTk1MWExMjUxOWU2YzJhOWEyZGY5ZDIxMzJjYTQ2NzU2MjI0MDBjMzVjZDMwMWJlODkyMQ
↑ https://www.ttl.fi/file-download/download/public/6517

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. doi:10.1515/znb-2004-0110. S2CID 46154131.
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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[1] "Chloramine-T hydrate". Sigma-Aldrich.

[CR-2] 1 2 3 Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo reagents". Chemical Reviews. 78: 65–79. doi:10.1021/cr60311a005.

[2022review-3] Nayak, Yogeesha N.; Gaonkar, Santosh L.; Saleh, Ebraheem Abdu Musad; Dawsari, Abdullah Mohammed A. L.; Harshitha; Husain, Kakul; Hassan, Ismail (2022-03-01). "Chloramine-T (N-chloro-p-toluenesulfonamide sodium salt), a versatile reagent in organic synthesis and analytical chemistry: An up to date review". Journal of Saudi Chemical Society. 26 (2): 101416. doi: 10.1016/j.jscs.2021.101416 . ISSN 1319-6103.

[4] Bodkin, J. A.; McLeod, M. D. (2002). "The Sharpless asymmetric aminohydroxylation". J. Chem. Soc., Perkin Trans. 1. 2002 (24): 2733–2746. doi:10.1039/b111276g.

[ueoic-5] Ura, Yasukazu; Sakata, Gozyo (2007). "Chloroamines". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553. ISBN 978-3-527-30673-2.

[Radiochemistry-6] Rösch, F. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Vol. 4. Dordrecht, Boston, London: Kluwer Academic Publishers.

[Keskinen1995-7] 1 2 https://www.duodecimlehti.fi/duo50224

[8] "Sactiv Kloramiini 1l". www.sillasiisti.fi (in Finnish). Retrieved 2024-10-25.

[9] ttps://www.carlroth.com/medias/SDB-0271-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMDc2NDF8YXBwbGljYXRpb24vcGRmfGgwYi9oZjEvOTE0MzI0MzgwMDYwNi9TREJfMDI3MV9HQl9FTi5wZGZ8NzE3ODFiZjc3YjFlZTk1MWExMjUxOWU2YzJhOWEyZGY5ZDIxMzJjYTQ2NzU2MjI0MDBjMzVjZDMwMWJlODkyMQ

[10] ttps://www.ttl.fi/file-download/download/public/6517

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v t e Antiseptics and disinfectants (D08)
Acridine derivatives	Ethacridine lactate 9-Aminoacridine Euflavine
Biguanides and amidines	Dibrompropamidine Chlorhexidine ^# Propamidine Hexamidine Polihexanide
Phenol and derivatives	Hexachlorophene Policresulen Phenol Triclosan Triclocarban Chloroxylenol ^# Biphenylol Fenticlor
Nitrofuran derivatives	Nitrofurazone
Iodine products	Iodine/octylphenoxypolyglycolether Povidone-iodine ^# Diiodohydroxypropane
Quinoline derivatives	Dequalinium Chlorquinaldol Oxyquinoline Clioquinol
Quaternary ammonium compounds	Benzalkonium Benzethonium chloride Cetrimonium (bromide/chloride) Cetylpyridinium Cetrimide Benzoxonium chloride Didecyldimethylammonium chloride
Mercurial products	Mercuric amidochloride Phenylmercuric borate Mercuric chloride Merbromin Nitromersol Thiomersal Mercuric iodide
Silver compounds	Silver nitrate
Alcohols	Propanol (propyl alcohol) Isopropanol (isopropyl alcohol) Ethanol (ethyl alcohol) ^#
Other	Potassium permanganate Sodium hypochlorite Halazone Monalazone Hydrogen peroxide Eosin Chloramine-T (tosylchloramide) Octenidine dihydrochloride
^# WHO-EM ^‡ Withdrawn from market Clinical trials: ^† Phase III ^§Never to phase III

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 at130 °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