| Revision as of 15:34, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473055715 of page Chloramine-T for the Chem/Drugbox validation project (updated: 'ChEMBL', 'ChEBI', 'StdInChI', 'StdInChIKey'). |
Latest revision as of 09:55, 25 October 2024 edit Ecangola (talk | contribs)Extended confirmed users93,554 edits →Disinfectant: fmtTag: Visual edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 460029231 |
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| verifiedrevid = 477379059 |
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| ImageFile = Chloramine T.svg |
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| ImageFile = Chloramine T.svg |
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| ImageFile1 = Chloramine-T-3D-balls.png |
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| ImageSize = 200px |
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| ImageAlt1 = Ball-and-stick model of the component ions of chloramine-T |
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| IUPACName = ''N''-chloro 4-methylbenzenesulfonamide, sodium salt |
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| ImageFile2 = Chloramin T trihydrát.jpg |
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| OtherNames = ''N''-chloro ''para''-toluenesulfonylamide,<br>sodium chloroazanide, chloramine-T |
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| ImageAlt2 = Chloramine-T trihydrate |
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| Section1 = {{Chembox Identifiers |
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| PIN = Sodium chloro(4-methylbenzene-1-sulfonyl)azanide |
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| OtherNames = {{bulletedlist|''N''-Chloro-''para''-toluenesulfonylamide|Sodium ''N''-chloro-4-methylbenzenesulphonomite|Chloraseptin|Chlorazol|Clorina|Disifin|Halamid|Hydroclonazone|Trichlorol|Minachlor|Tosylchloramide Sodium|''N''-chlorotosylamide, sodium salt}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2876055 |
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| ChemSpiderID = 2876055 |
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| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID2 = 29119 |
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| ChemSpiderID2 = 29119 |
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| ChemSpiderID2_Comment = (free acid) |
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| ChemSpiderID2_Comment = (free acid) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4IU6VSV0EI |
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| UNII = 328AS34YM6 |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 =4IU6VSV0EI |
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| UNII1_Comment = (trihydrate) |
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| EINECS = 204-854-7 |
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| InChI = 1/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1 |
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| InChI = 1/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1 |
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| InChIKey = VDQQXEISLMTGAB-UHFFFAOYAP |
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| InChIKey = VDQQXEISLMTGAB-UHFFFAOYAP |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 127-65-1 |
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| CASNo = 127-65-1 |
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| CASNo2_Ref = {{cascite|correct|??}} |
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| CASNo2 = 7080-50-4 |
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| CASNo2 = 7080-50-4 |
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| CASNo2_Comment = (trihydrate) |
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| CASNo2_Comment = (trihydrate) |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1697734 --> |
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| ChEMBL = 1697734 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 53767 |
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| ChEBI = 53782 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1 |
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| StdInChI = 1S/C7H8ClNO2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = VDQQXEISLMTGAB-UHFFFAOYSA-N |
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| StdInChIKey = NXTVQNIVUKXOIL-UHFFFAOYSA-N |
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| PubChem = 10198484 |
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| PubChem = 3641960 |
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| PubChem2 = 31388 |
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| PubChem2 = 31388 |
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| PubChem2_Comment = (free acid) |
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| PubChem2_Comment = (free acid) |
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| KEGG = D02445 |
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| KEGG = D02445 |
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| SMILES = .O=S(=O)(Cl)c1ccc(cc1)C |
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| SMILES = .O=S(=O)(Cl)c1ccc(cc1)C |
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}} |
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|Section2={{Chembox Properties |
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| Formula = C<sub>7</sub>H<sub>7</sub>ClNO<sub>2</sub>S·Na<br />C<sub>7</sub>H<sub>7</sub>ClNO<sub>2</sub>S·Na·(3H<sub>2</sub>O) (hydrate) |
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| MolarMass = 227.64 g/mol <br />281.69 g/mol (trihydrate) |
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| Appearance = White powder |
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| Density = 1.4 g/cm<sup>3</sup> |
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| MeltingPt = Releases chlorine at |
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| MeltingPtC = 130 |
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| MeltingPt_notes = <br />Solid melts at 167–169 °C |
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| BoilingPt = |
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| Solubility = >100 g/L (hydrate)<ref>{{cite web | url = http://www.sigmaaldrich.com/catalog/product/sigma/c9887?lang=en | title = Chloramine-T hydrate | publisher = ]}}</ref> |
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}} |
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|Section6={{Chembox Pharmacology |
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| ATCCode_prefix = D08 |
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| ATCCode_prefix = D08 |
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| ATCCode_suffix = AX04 |
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| ATCCode_suffix = AX04 |
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| ATC_Supplemental = {{ATCvet|P53|AB04}} |
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| ATC_Supplemental = {{ATCvet|P53|AB04}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section7={{Chembox Hazards |
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| MainHazards = Corrosive |
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| Formula = C<sub>7</sub>H<sub>7</sub>ClNO<sub>2</sub>S·Na (3H<sub>2</sub>O) |
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| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}} |
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| MolarMass = 227.64 g/mol |
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| GHSSignalWord = Danger |
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| Appearance = white powder |
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| HPhrases = {{H-phrases|302|314|334}} |
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| Density = 1.4 g/cm³ |
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| PPhrases = {{P-phrases|260|261|264|270|280|285|301+312|301+330+331|303+361+353|304+340|304+341|305+351+338|310|321|330|342+311|363|405|501}} |
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| MeltingPt = releases chlorine at 130 °C<br>solid melts at 167–169 °C |
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| BoilingPt = |
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| FlashPt = |
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| AutoignitionPt = |
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| Solubility = 15% in water (25 °C)<br>7.5% in rectified spirit (20 °C)<br>insoluble in benzene and ethers |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Corrosive |
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| RPhrases = {{R22}} {{R31}} {{R34}} {{R42}} |
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| SPhrases = {{S1/2}} {{S7}} {{S22}} {{S26}} {{S36/37/39}} {{S45}} |
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| FlashPt = |
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| Autoignition = |
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}} |
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'''Chloramine-T''' is the ] with the formula CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>NClNa. Both the anhydrous salt and its trihydrate are known. Both are white powders. Chloramine-T is used as a reagent in ].<ref name=CR>{{cite journal|doi=10.1021/cr60311a005|title=Chloramine T and Related ''N''-halogeno-''N''-metallo reagents|journal=Chemical Reviews|volume=78|pages=65–79|year=1978|last1=Campbell|first1=Malcolm M.|last2=Johnson|first2=Graham.}}</ref> It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles.<ref name=2022review>{{Cite journal |last1=Nayak |first1=Yogeesha N. |last2=Gaonkar |first2=Santosh L. |last3=Saleh |first3=Ebraheem Abdu Musad |last4=Dawsari |first4=Abdullah Mohammed A. L. |last5=Harshitha |last6=Husain |first6=Kakul |last7=Hassan |first7=Ismail |date=2022-03-01 |title=Chloramine-T (N-chloro-p-toluenesulfonamide sodium salt), a versatile reagent in organic synthesis and analytical chemistry: An up to date review |journal=Journal of Saudi Chemical Society |language=en |volume=26 |issue=2 |pages=101416 |doi=10.1016/j.jscs.2021.101416 |issn=1319-6103|doi-access=free }}</ref> It's inexpensive, has low toxicity and acts as a oxidizing agent. In addition, it also acts as a source of nitrogen anions and electrophilic cations. It may undergo degradation on long term exposure to atmosphere such that care must be taken during its storage. |
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==Reactions== |
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Chloramine-T contains active (]) ]. Its reactivity is similar to that of ]. Aqueous solutions of chloramine-T are slightly basic (] typically 8.5). The ] of the closely related ''N''-chlorophenylsulfonamide C<sub>6</sub>H<sub>5</sub>SO<sub>2</sub>NClH is 9.5.<ref name=CR/> |
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It is prepared by oxidation of toluenesulfonamide with sodium hypochlorite, with the latter being produced '']'' from ] and chlorine (Cl<sub>2</sub>):<ref name=CR/> |
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] |
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==Uses== |
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===Reagent in amidohydroxylation=== |
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The ] converts an alkene to a vicinal ]. A common source of the amido component of this reaction is chloramine-T.<ref>{{cite journal|last1=Bodkin |first1=J. A. |last2=McLeod |first2=M. D. |title=The Sharpless asymmetric aminohydroxylation |journal=J. Chem. Soc., Perkin Trans. 1 |date=2002 |volume=2002 |issue=24 |pages=2733–2746 |doi=10.1039/b111276g}}</ref> Vicinal aminoalcohols are important products in ] and recurring ]s in ]. |
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:] |
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===Oxidant=== |
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Chloramine-T is a strong oxidant.{{Contradictory inline|section=Introduction|date=September 2022}} It oxidizes ] to sulfur and ] to yield a harmless crystalline ].<ref name="ueoic">{{Ullmann| first1=Yasukazu|last1=Ura|first2=Gozyo|last2=Sakata|title=Chloroamines|year=2007|doi=10.1002/14356007.a06_553}}</ref> |
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It converts ] to ] (ICl). ICl rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid ]. Thus, chloramine-T is used to incorporate iodine into peptides and proteins. Chloramine-T together with ] or ] is commonly used for ] peptides and proteins with ] isotopes.<ref name=Radiochemistry>{{cite book | first= F.|last=Rösch | title = Radiochemistry and Radiopharmaceutical Chemistry in Life Sciences |volume=4 | publisher = Kluwer Academic Publishers | location = Dordrecht, Boston, London }}</ref> |
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===Disinfectant=== |
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Chloramine-T has a long history as a hospital disinfectant. It is effective against e.g. hepatitis and HI viruses.<ref name="Keskinen1995">https://www.duodecimlehti.fi/duo50224</ref> Unlike the more common ], chloramine-T is mildly basic, almost odorless and is not a ].<ref>{{Cite web |title=Sactiv Kloramiini 1l |url=https://www.sillasiisti.fi/sactiv-kloramiini-1l |access-date=2024-10-25 |website=www.sillasiisti.fi |language=fi}}</ref> |
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==Safety== |
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Chloramine-T is harmful if swallowed. It is corrosive on skin, eyes or mucous membranes. It releases toxic ] upon reaction with acids. It is water-soluble and thus can be released to the environment dissolved in water. It is a known sensitizer.<ref>https://www.carlroth.com/medias/SDB-0271-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMDc2NDF8YXBwbGljYXRpb24vcGRmfGgwYi9oZjEvOTE0MzI0MzgwMDYwNi9TREJfMDI3MV9HQl9FTi5wZGZ8NzE3ODFiZjc3YjFlZTk1MWExMjUxOWU2YzJhOWEyZGY5ZDIxMzJjYTQ2NzU2MjI0MDBjMzVjZDMwMWJlODkyMQ</ref> Chloramine-T has been observed to cause ] and flu-like symptoms.<ref name="Keskinen1995" /><ref>https://www.ttl.fi/file-download/download/public/6517</ref> |
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==Certifications== |
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* ] 1276 Bactericidal |
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* EN 13713 Bactericidal |
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* EN 14675 Virucidal |
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* EN 14476 Virucidal ] |
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* EN 1650 Fungicidal |
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* EN 13704 Sporicidal '']'' |
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==References== |
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{{reflist}} |
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{{More citations needed|date=November 2011}} |
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==External links== |
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* {{cite journal|author=M. Shetty, T. B. Gowda|s2cid=46154131|title=A Study of Substituent Effect on the Oxidative Strengths of N-Chloroarenesulphonamides: Kinetics of Oxidation of Leucine and Isoleucine in Aqueous Acid Medium|journal=Zeitschrift für Naturforschung|year=2004|volume=59|pages=63–72|doi=10.1515/znb-2004-0110}} |
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* Chemicalland21.com: |
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* InChem.org: |
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* {{cite web |url=http://www.disifinusa.com |title=Disifin USA |accessdate=2010-02-09 |url-status=dead |archiveurl=https://web.archive.org/web/20091225181638/http://disifinusa.com/ |archivedate=2009-12-25 }} |
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{{Antiseptics and disinfectants}} |
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{{Authority control}} |
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