Revision 421825442 of "Chloramine-T" on enwiki

{{chembox
| Verifiedfields = changed
| verifiedrevid = 388653250
| ImageFile = Chloramine T.svg
| ImageSize = 200px
| IUPACName = ''N''-chloro 4-methylbenzenesulfonamide, sodium salt
| OtherNames = ''N''-chloro ''para''-toluenesulfonylamide,<br>sodium chloro[(4-methyl phenyl)sulfonyl]azanide, chloramine-T
| Section1 = {{Chembox Identifiers
|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2876055
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4IU6VSV0EI
| InChI = 1/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1
| InChIKey = VDQQXEISLMTGAB-UHFFFAOYAP
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 127-65-1
|   PubChem = 10198484
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D02445
|   SMILES = [Na+].O=S(=O)([N-]Cl)c1ccc(cc1)C
}}
| Section2 = {{Chembox Properties
|   Formula = C<sub>7</sub>H<sub>7</sub>ClNO<sub>2</sub>S·Na (3H<sub>2</sub>O)
|   MolarMass = 227.64
|   Appearance = white powder
|   Density = 1.4 g/cm³
|   MeltingPt = releases chlorine at 130 °C<br>solid melts at 167–169 °C
|   BoilingPt = 
|   Solubility = 15% in water (25 °C)<br>7.5% in rectified spirit (20 °C)<br>insoluble in benzene and ethers
  }}
| Section3 = {{Chembox Hazards
|   MainHazards = Corrosive
|   RPhrases = 22-31-34-42
|   SPhrases = (1/2-)-7-22-26-36/37/39-45
|   FlashPt = 
|   Autoignition = 
  }}
}}
''' ''N''-chloro tosylamide''' sodium salt, sold as '''chloramine-T''', is a ''[[Nitrogen|N]]''-[[Chlorine|chlorinated]] and ''[[Nitrogen|N]]''-[[Deprotonation|deprotonated]] [[Sulfonamide (chemistry)|sulfonamide]] used as a [[biocide]] and a mild [[disinfectant]]. It is a white powder that gives unstable solutions with water.

==Chemistry==
As an ''N''-chloro compound, it contains active ([[electrophilic]]) [[chlorine]] and can be compared to the ''[[Oxygen|O]]''-chlorinated [[sodium hypochlorite]]. Chloramine-T is nearly neutral (pH typically 8.5). In water, it breaks down to the disinfectant [[hypochlorite]]. It can be used as a source of electrophilic chlorine in [[organic synthesis]].

The sulfur adjacent to the nitrogen can stabilize a nitrogen anion (R<sub>2</sub>N<sup>–</sup>), so that the N-chloro sulfonamide moiety can be deprotonated at nitrogen even with only sodium hydroxide.

==Use in radioiodination==
If iodide anion is present in the solution, released hypochlorite acts as effective oxidizing agent to form iodine chloride (ICl). ICl rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of tyrosine aminoacid. Thus, Chloramine-T is widely used for the incorporation of iodine to peptides and proteins. Chloramine-T (together with Iodogen or lactoperoxidase) is commonly used for labeling peptides and proteins with radioiodine isotopes(I-123, I-125 or I-131) <ref name=Radiochemistry>{{Cite encyclopedia | author = F.Rösch | title = Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4 | publisher = Kluwer Academic Publishers | location = Dordrecht/Boston/London | 10.1002/14356007.a14_381}}</ref>

==Use as a biocide==
Chloramine-T is used for disinfection and as an [[algicide]], [[bactericide]], [[germicide]], for [[parasite]] control, and for drinking water disinfection. The molecular structure of toluenesulfonylamide is similar to [[para-aminobenzoic acid]], an intermediate in bacterial metabolism, which is disrupted by this sulfonamide (in the same way as by a [[sulfa drug]]). Therefore, chloramine-T is capable of inhibiting with bacterial growth with two mechanisms, with the phenylsulfonamide moiety and the electrophilic chlorine.

==References==
{{reflist}}

==External links==
*Chemicalland21.com: [http://chemicalland21.com/lifescience/agro/CHLORAMINE%20T.htm]
*MSDS [http://www.hschem.com/msdscht.html], ICSS [http://www.inchem.org/documents/icsc/icsc/eics0413.htm]

[[Category:Sulfonamides]]
[[Category:Pesticides]]

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[[ja:クロラミンT]]
[[fi:Kloramiini]]
[[pl:Chloramina T]]
[[es: Cloramina T]]