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 at 130 °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

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.^{[contradictory]} It oxidizes hydrogen sulfide to sulfur and mustard gas 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. Thus, chloramine-T is used to incorporate iodine into peptides and proteins. Chloramine-T together with iodogen 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.
^ ^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.
^ 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 978-3527306732.
^ Rösch, F. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Vol. 4. Dordrecht, Boston, London: Kluwer Academic Publishers.
^ ^a ^b 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.

[1] "Chloramine-T hydrate". Sigma-Aldrich.

[CR-2] 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 978-3527306732.

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

[Keskinen1995-7] ttps://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

[2]

[3]

[1]

[4]

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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