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. Th ...

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 car ...

)

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 ...

. 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 Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkal ...

and chlorine (Cl₂): Synthesis Chloramine T

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 dio ...

converts an alkene to a vicinal aminoalcohol. A common source of the amido component of this reaction is chloramine-T. Vicinal aminoalcohols are important products in

and recurring pharmacophores in

drug discovery In the fields of medicine, biotechnology and pharmacology, drug discovery is the process by which new candidate medications are discovered. Historically, drugs were discovered by identifying the active ingredient from traditional remedies or by ...

. :

Oxidant

Chloramine-T is a strong oxidant. It oxidizes

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The und ...

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 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 def ...

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 pola ...

(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 Gr ...

. 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 deve ...

* 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