Tosylchloramide: Difference between revisions

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Tosylchloramide
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
CAS Number	127-65-1 ; 7080-50-4 (trihydrate) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:53782 ;
ChEMBL	ChEMBL1697734 ;
ChemSpider	2876055 ; 29119 (free acid) ;
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	D02445 ;
PubChem CID	10198484; 31388 (free acid);
UNII	328AS34YM6 ; 4IU6VSV0EI (trihydrate) ;
	InChI InChI=1S/C7H8ClNO2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,1H3 Key: NXTVQNIVUKXOIL-UHFFFAOYSA-N ; InChI=1/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1 Key: VDQQXEISLMTGAB-UHFFFAOYAP;
	SMILES [Na+].O=S(=O)([N-]Cl)c1ccc(cc1)C;
Properties
Chemical formula	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).
	verify (what is ?)
	Infobox references

VisualWikitext

Latest revision as of 18:45, 14 April 2015

Template:Chembox E number Template:Chembox Appearance Template:Chembox Density Template:Chembox MeltingPt Template:Chembox SolubilityInWater Template:Chembox MainHazards Template:Chembox RPhrases Template:Chembox SPhrases

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

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).^[1]

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.^[2]

Certifications

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

References

↑ F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4. Dordrecht/Boston/London: Kluwer Academic Publishers.
↑ Yasukazu Ura; Gozyo Sakata (2007), "Chloroamines", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5

External links

Chemicalland21.com: Chloramine T (Tosylchloramide sodium)
InChem.org: Chloramine T
"Disifin USA". Retrieved 2010-02-09.

Template:Antiseptics and disinfectants

[Radiochemistry-1] F.Rösch. Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences. Volume 4. Dordrecht/Boston/London: Kluwer Academic Publishers.

[ueoic-2] Yasukazu Ura; Gozyo Sakata (2007), "Chloroamines", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5

[1]

[2]

@@ Line 1: / Line 1: @@
+{{chembox
+| Verifiedfields = changed
-{{Chembox new
+| Watchedfields = changed
-|ImageFile=Tosylchloramide.png
+| verifiedrevid = 477379059
-|ImageSize=
+| ImageFile = Chloramine_T.png
-|IUPACName=N-chloro-4-methylbenzenesulfonamide
+| ImageSize = 200px
-|OtherNames=
+| ImageFile1 = Chloramine-T-3D-balls.png
-|Section1= {{Chembox Identifiers
+| ImageSize1 = 200px
-|  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
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 2876055
+| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID2 = 29119
+| ChemSpiderID2_Comment = (free acid)
+| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII = 328AS34YM6
+| 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
    }}
-|Section2= {{Chembox Properties
+| Section3 = {{Chembox Hazards
-|  Formula=C<sub>7</sub>H<sub>8</sub>ClNO<sub>2</sub>S
+|   MainHazards = Corrosive
-|  MolarMass=205.663
+|   RPhrases = {{R22}} {{R31}} {{R34}} {{R42}}
-|  Appearance=
+|   SPhrases = {{S1/2}} {{S7}} {{S22}} {{S26}} {{S36/37/39}} {{S45}}
-|  Density=
+|   FlashPt =
-|  MeltingPt=
+|   Autoignition =
-|  BoilingPt=
-|  Solubility=
-  }}
-|Section3= {{Chembox Hazards
-|  MainHazards=
-|  FlashPt=
-|  Autoignition=
    }}
 }}
+__NOTOC__
+{{SI}}
+{{CMG}}
-'''Tosylchloramide''' is an [[antiseptic]]/[[disinfectant]], often used as the sodium salt '''tosylchloramide sodium'''.
+==Overview==
+'''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.
+==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==
+* EN 13713 Bactericidal
+* EN 14675 Virucidal
+* EN 14476 Virucidal [[Norovirus]]
+* EN 1650  Fungicidal
+* EN 13704 Sporicidal [[Clostridium difficile]]
+==References==
+{{reflist|2}}
+==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}}
 [[Category:Antiseptics]]
+[[Category:Pesticides]]
+[[Category:Drug]]
 [[Category:Sulfonamides]]
+[[Category:Organochlorides]]
-{{pharmacology-stub}}
+[[Category:Sodium compounds]]
-{{WikiDoc Sources}}

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
CAS Number	127-65-1^Y 7080-50-4 (trihydrate)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:53782^N
ChEMBL	ChEMBL1697734^N
ChemSpider	2876055^Y 29119 (free acid)^Y
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	D02445^Y
PubChem CID	10198484 31388 (free acid)
UNII	328AS34YM6^N 4IU6VSV0EI (trihydrate)^N
InChI InChI=1S/C7H8ClNO2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,1H3^N Key: NXTVQNIVUKXOIL-UHFFFAOYSA-N^N InChI=1/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1 Key: VDQQXEISLMTGAB-UHFFFAOYAP
SMILES [Na+].O=S(=O)([N-]Cl)c1ccc(cc1)C
Properties
Chemical formula	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 ^YN ?)
Infobox references