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.[1] It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles.[2] 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.

## Contents

* 1 Reactions
* 2 Uses
* 2.1 Reagent in amidohydroxylation
* 2.2 Oxidant
* 2.3 Disinfectant
* 3 Safety
* 4 Certifications
* 5 References
* 6 External links

## 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.[1]

It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced in situ from sodium hydroxide and chlorine (Cl2):[1]

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## 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.[3] 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.[4]

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.[5]

### Disinfectant

Chloramine-T has a long history as a hospital disinfectant. It is effective against e.g. hepatitis and HI viruses.[6] Unlike the more common sodium hypochlorite, chloramine-T is mildly basic, almost odorless and is not a bleaching agent.[7]

## 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.[8] Chloramine-T has been observed to cause occupational asthma and flu-like symptoms.[6][9]

## Certifications

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

## References

1. ↑ 1.0 1.1 1.2 Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo reagents". Chemical Reviews 78: 65–79. doi:10.1021/cr60311a005.
2. ↑ 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" (in en). Journal of Saudi Chemical Society 26 (2). doi:10.1016/j.jscs.2021.101416. ISSN 1319-6103.
3. ↑ 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.
4. ↑ Ura, Yasukazu; Sakata, Gozyo (2007). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_553.
5. ↑ Rösch, F.. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. 4. Dordrecht, Boston, London: Kluwer Academic Publishers.
6. ↑ 6.0 6.1 "Kloramiini-T-jauheesta ammattiastmaa ja nuhaa välinehuoltotyössä" (in Fi). February 23, 1995. https://www.duodecimlehti.fi/duo50224.
7. ↑ "Sactiv Kloramiini 1l" (in fi). https://www.sillasiisti.fi/sactiv-kloramiini-1l.
8. ↑ https://www.carlroth.com/medias/SDB-0271-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMDc2NDF8YXBwbGljYXRpb24vcGRmfGgwYi9oZjEvOTE0MzI0MzgwMDYwNi9TREJfMDI3MV9HQl9FTi5wZGZ8NzE3ODFiZjc3YjFlZTk1MWExMjUxOWU2YzJhOWEyZGY5ZDIxMzJjYTQ2NzU2MjI0MDBjMzVjZDMwMWJlODkyMQ [bare URL]
9. ↑ https://www.ttl.fi/file-download/download/public/6517 [bare URL]

## 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.
* Chemicalland21.com: Chloramine T (Tosylchloramide sodium)
* InChem.org: Chloramine T
* "Disifin USA". http://www.disifinusa.com.

* 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
* 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

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