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{{chembox
 
| Verifiedfields = changed
{{Chembox new
| Watchedfields = changed
|ImageFile=Tosylchloramide.png
| verifiedrevid = 477379059
|ImageSize=
| ImageFile = Chloramine T.svg
|IUPACName=N-chloro-4-methylbenzenesulfonamide
| ImageSize = 200px
|OtherNames=
| ImageFile1 = Chloramine-T-3D-balls.png
|Section1= {{Chembox Identifiers
| ImageSize1 = 200
| CASNo=127-65-1  
| ImageAlt1 = Ball-and-stick model of the component ions of chloramine-T
| PubChem=31388
| IUPACName = ''N''-chloro 4-methylbenzenesulfonamide, sodium salt
| SMILES=CC1=CC=C(C=C1)S(=O)(=O)NCl
| OtherNames = ''N''-chloro ''para''-toluenesulfonylamide,<br>sodium chloro[(4-methyl phenyl)sulfonyl]azanide, chloramine-T
  }}
| Section1 = {{Chembox Identifiers
|Section2= {{Chembox Properties
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| Formula=C<sub>7</sub>H<sub>8</sub>ClNO<sub>2</sub>S
| ChemSpiderID = 2876055
| MolarMass=205.663
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| Appearance=
| ChemSpiderID2 = 29119
| Density=
| ChemSpiderID2_Comment = (free acid)
| MeltingPt=
| UNII_Ref = {{fdacite|changed|FDA}}
| BoilingPt=
| UNII = 328AS34YM6
| Solubility=
| UNII2_Ref = {{fdacite|changed|FDA}}
| UNII2 = 4IU6VSV0EI
| UNII2_Comment = (trihydrate)
| 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
| CASNo2_Ref = {{cascite|correct|??}}
| CASNo2 = 7080-50-4
| CASNo2_Comment = (trihydrate)
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1697734
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 53782
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C7H8ClNO2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NXTVQNIVUKXOIL-UHFFFAOYSA-N
| PubChem = 10198484
| PubChem2 = 31388
| PubChem2_Comment = (free acid)
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02445
| SMILES = [Na+].O=S(=O)([N-]Cl)c1ccc(cc1)C
| ATCCode_prefix = D08
| ATCCode_suffix = AX04
| ATC_Supplemental = {{ATCvet|P53|AB04}}
}}
| 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 g/mol in usual tri-hydrated form 282 Daltons.
|   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
| Section3 = {{Chembox Hazards
| MainHazards=
|   MainHazards = Corrosive
| FlashPt=
|   RPhrases = {{R22}} {{R31}} {{R34}} {{R42}}
| Autoignition=
|  SPhrases = {{S1/2}} {{S7}} {{S22}} {{S26}} {{S36/37/39}} {{S45}}
|  FlashPt =  
|   Autoignition =  
   }}
   }}
}}
}}
'''Tosylchloramide''' or ''' ''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. Trade names of chloramine-T products include '''Chloraseptin''', '''Chlorazol''', '''Clorina''', '''Disifin''', '''Halamid''', '''Hydroclonazone''', '''Trichlorol''', '''Minachlor''', and generic '''Chloramin T''' or '''Tosylchloramide Sodium''', among others.
==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 slightly basic (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 anionic sulfonamide is stabilized by delocalization of the nitrogen lone pair across the SO<sub>2</sub> group, facilitating deprotonation of the parent amine by bases such as hydroxide. It is readily [[biodegradable]] by use of [[ultraviolet]] (UV) light.
===Synthesis===
Chloramine-T is prepared from ''p''-toluenesulfonamide and sodium hypochlorite, with the latter being produced ''[[in situ]]'' from [[sodium hydroxide]] and chlorine (Cl<sub>2</sub>).<ref name="shetty">M. Shetty, T. B. Gowda, ''A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium'', in: ''Zeitschrift für Naturforschung'' '''2004''', ''59'', 63–72.</ref>
[[File:Synthesis Chloramine T.svg|450px]]
==Uses==
===Iodination and radioiodination===
Hypochlorite released from chloramine-T acts as an effective [[oxidizing agent]] for [[iodide]] to form [[iodine monochloride]] (ICl). ICl rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid [[tyrosine]]. 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 [[Isotopic labeling|labeling]] peptides and proteins with [[radioiodine]] isotopes ([[Iodine-123|<sup>123</sup>I]], [[Iodine-125|<sup>125</sup>I]] or [[Iodine-131|<sup>131</sup>I]]).<ref name=Radiochemistry>{{cite book | author = F.Rösch | title = Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4 | publisher = Kluwer Academic Publishers | location = Dordrecht/Boston/London }}</ref>
===Biocide===
Chloramine-T is available in tablet or powder form and has to be dissolved before use. It is sprayed on a surface and allowed to stand for at least 15 minutes before being wiped off or allowed to dry. It used in areas such as [[hospitals]], [[laboratories]], [[nursing homes]], [[funeral homes]], [[medical]], [[Dentistry|dental]] and [[veterinary]] facilities, where control of [[pathogens]] is required, for disinfecting surfaces and soaking medical and dental equipment. The substance is also used for [[parasite]] control and for drinking water disinfection.
Chloramine-T is as an [[algicide]], [[bactericide]], [[virucide]], [[fungicide]] (including [[spores]]), [[germicide]]. It is also effective against [[mycobacteria]] such as [[tuberculosis]], [[foot-and-mouth disease]] and [[avian influenza]]. 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 hypochlorite, which destroys the [[DNA]] structure via oxidation and thereby prevents microbes from reproducing and reforming.
===Protective agent===
Chloramine-T reacts readily with [[mustard gas]] to yield a harmless crystalline [[sulfimide]]; chloramine-T derivatives are being studied as protective agents against [[poison gas]].<ref name="ueoic">{{citation | author=Yasukazu Ura | author2=Gozyo Sakata | contribution=Chloroamines | title=[[Ullmann's Encyclopedia of Industrial Chemistry]] | edition=7th | publisher=Wiley | year=2007 | page=5}}</ref>
==Certifications==
*[[List of EN standards|EN]] 1276  Bactericidal
* EN 13713 Bactericidal
* EN 14675 Virucidal
* EN 14476 Virucidal [[Norovirus]]
* EN 1650  Fungicidal
* EN 13704 Sporicidal [[Clostridium difficile]]
==References==
{{reflist}}
{{Refimprove|date=November 2011}}


'''Tosylchloramide''' is an [[antiseptic]]/[[disinfectant]], often used as the sodium salt '''tosylchloramide sodium'''.
==External links==
* Chemicalland21.com: [http://chemicalland21.com/lifescience/agro/CHLORAMINE%20T.htm Chloramine T (Tosylchloramide sodium)]
* InChem.org: [http://www.inchem.org/documents/icsc/icsc/eics0413.htm Chloramine T]
* {{cite web |url=http://www.disifinusa.com |title=Disifin USA |accessdate=2010-02-09 |work=}}


{{Antiseptics and disinfectants}}
{{Antiseptics and disinfectants}}


[[Category:Antiseptics]]
[[Category:Antiseptics]]
[[Category:Pesticides]]
[[Category:Sulfonamides]]
[[Category:Sulfonamides]]
 
[[Category:Organochlorides]]
{{pharmacology-stub}}
[[Category:Sodium compounds]]
{{WikiDoc Sources}}

Revision as of 15:22, 14 April 2015

Template:Chembox E numberTemplate:Chembox AppearanceTemplate:Chembox DensityTemplate:Chembox MeltingPtTemplate:Chembox SolubilityInWaterTemplate:Chembox MainHazardsTemplate:Chembox RPhrasesTemplate:Chembox SPhrases
Tosylchloramide
File:Chloramine T.svg
Ball-and-stick model of the component ions of chloramine-T
Names
IUPAC name
N-chloro 4-methylbenzenesulfonamide, sodium salt
Other names
N-chloro para-toluenesulfonylamide,
sodium chloro[(4-methyl phenyl)sulfonyl]azanide, chloramine-T
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG
UNII
Properties
C7H7ClNO2S·Na (3H2O)
Molar mass 227.64 g/mol in usual tri-hydrated form 282 Daltons.
Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

Tosylchloramide or N-chloro tosylamide, sodium salt, sold as chloramine-T, is a N-chlorinated and N-deprotonated sulfonamide used as a biocide and a mild disinfectant. It is a white powder that gives unstable solutions with water. Trade names of chloramine-T products include Chloraseptin, Chlorazol, Clorina, Disifin, Halamid, Hydroclonazone, Trichlorol, Minachlor, and generic Chloramin T or Tosylchloramide Sodium, among others.

Chemistry

As an N-chloro compound, it contains active (electrophilic) chlorine and can be compared to the O-chlorinated sodium hypochlorite. Chloramine-T is slightly basic (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 anionic sulfonamide is stabilized by delocalization of the nitrogen lone pair across the SO2 group, facilitating deprotonation of the parent amine by bases such as hydroxide. It is readily biodegradable by use of ultraviolet (UV) light.

Synthesis

Chloramine-T is prepared from p-toluenesulfonamide and sodium hypochlorite, with the latter being produced in situ from sodium hydroxide and chlorine (Cl2).[1]

File:Synthesis Chloramine T.svg

Uses

Iodination and radioiodination

Hypochlorite released from chloramine-T acts as an effective oxidizing agent for iodide to form iodine monochloride (ICl). ICl rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid tyrosine. 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 (123I, 125I or 131I).[2]

Biocide

Chloramine-T is available in tablet or powder form and has to be dissolved before use. It is sprayed on a surface and allowed to stand for at least 15 minutes before being wiped off or allowed to dry. It used in areas such as hospitals, laboratories, nursing homes, funeral homes, medical, dental and veterinary facilities, where control of pathogens is required, for disinfecting surfaces and soaking medical and dental equipment. The substance is also used for parasite control and for drinking water disinfection.

Chloramine-T is as an algicide, bactericide, virucide, fungicide (including spores), germicide. It is also effective against mycobacteria such as tuberculosis, foot-and-mouth disease and avian influenza. 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 hypochlorite, which destroys the DNA structure via oxidation and thereby prevents microbes from reproducing and reforming.

Protective agent

Chloramine-T reacts readily with mustard gas to yield a harmless crystalline sulfimide; chloramine-T derivatives are being studied as protective agents against poison gas.[3]

Certifications

References

  1. ↑ M. Shetty, T. B. Gowda, A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium, in: Zeitschrift für Naturforschung 2004, 59, 63–72.
  2. ↑ F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4. Dordrecht/Boston/London: Kluwer Academic Publishers.
  3. ↑ Yasukazu Ura; Gozyo Sakata (2007), "Chloroamines", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5

External links

Template:Antiseptics and disinfectants

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