Chloramine-T is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

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. 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)

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 i ...

. 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 s ...

. 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): Synthesis Chloramine T

Uses

Reagent in amidohydroxylation

The Sharpless oxyamination 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 and recurring

pharmacophore 300px, An example of a pharmacophore model. A pharmacophore is an abstract description of molecular features that are necessary for molecular recognition of a ligand by a biological macromolecule. IUPAC defines a pharmacophore to be "an ensemble o ...

s in drug discovery. :

Oxidant

Chloramine-T is a strong oxidant. It oxidizes hydrogen sulfide to sulfur and mustard gas to yield a harmless crystalline sulfimide. It converts

iodide An iodide ion is the ion I−. Compounds with iodine in formal oxidation state −1 are called iodides. In everyday life, iodide is most commonly encountered as a component of iodized salt, which many governments mandate. Worldwide, iodine de ...

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 an ...

(ICl). ICl rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid

tyrosine -Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the G ...

. Thus, chloramine-T is used to incorporate iodine into peptides and proteins. Chloramine-T together with iodogen or

lactoperoxidase Lactoperoxidase is a peroxidase enzyme secreted from mammary, salivary and other mucosal glands including the lungs, bronchii and nose that functions as a natural and the first line of defense against bacteria and viruses. Lactoperoxidase is a m ...

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 Norovirus, sometimes referred to as the winter vomiting disease, is the most common cause of gastroenteritis. Infection is characterized by non-bloody diarrhea, vomiting, and stomach pain. Fever or headaches may also occur. Symptoms usually devel ...

* 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