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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 Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
. It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles. It's a inexpensive, low toxic and mild oxidizing agent, and it also acts as a source of nitrogen anions and eletrophilic cations. But it may undergo degradation on long term exposure to atmosphere, so care must be taken during the storage.


Reactions

Chloramine-T contains active (
electrophilic In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carri ...
)
chlorine Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is ...
. Its reactivity is similar to that of
sodium hypochlorite Sodium hypochlorite (commonly known in a dilute solution as bleach) is an inorganic chemical compound with the formula NaOCl (or NaClO), comprising a sodium cation () and a hypochlorite anion (or ). It may also be viewed as the sodium salt of h ...
. Aqueous solutions of chloramine-T are slightly basic ( pH typically 8.5). The p''K''a of the closely related ''N''-chlorophenylsulfonamide C6H5SO2NClH is 9.5. It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced ''
in situ ''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premises", or "in place" to describe where an event takes place and is used in ...
'' from sodium hydroxide and chlorine (Cl2):


Uses


Reagent in amidohydroxylation

The
Sharpless oxyamination The Sharpless oxyamination (often known as Sharpless aminohydroxylation) is the chemical reaction that converts an alkene to a vicinal amino alcohol. The reaction is related to the Sharpless dihydroxylation, which converts alkenes to vicinal diols ...
converts an alkene to a vicinal
aminoalcohol In organic chemistry, alkanolamines are organic compounds that contain both hydroxyl () and amino (, , and ) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification. Meth ...
. A common source of the amido component of this reaction is chloramine-T. Vicinal aminoalcohols are important products in
organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
and recurring pharmacophores in drug discovery. :


Oxidant

Chloramine-T is a strong oxidant. It oxidizes hydrogen sulfide to sulfur and
mustard gas Mustard gas or sulfur mustard is a chemical compound belonging to a family of cytotoxic and blister agents known as mustard agents. The name ''mustard gas'' is technically incorrect: the substance, when dispersed, is often not actually a gas, b ...
to yield a harmless crystalline sulfimide. It converts iodide to
iodine monochloride Iodine monochloride is an interhalogen compound with the formula . It is a red-brown chemical compound that melts near room temperature. Because of the difference in the electronegativity of iodine and chlorine, this molecule is highly polar a ...
(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 Labelling or using a label is describing someone or something in a word or short phrase. For example, the label "criminal" may be used to describe someone who has broken a law. Labelling theory is a theory in sociology which ascribes labelling ...
peptides and proteins with
radioiodine There are 37 known isotopes of iodine (53I) from 108I to 144I; all undergo radioactive decay except 127I, which is stable. Iodine is thus a monoisotopic element. Its longest-lived radioactive isotope, 129I, has a half-life of 15.7 million year ...
isotopes.


Certifications

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


References


External links

* * Chemicalland21.com
Chloramine T (Tosylchloramide sodium)
* InChem.org

* {{Antiseptics and disinfectants Antiseptics Pesticides Sulfonamides Organochlorides Organic sodium salts p-Tosyl compounds Nitrogen–halogen compounds Sulfur–nitrogen compounds