| Revision as of 18:23, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464762334 of page 4-Toluenesulfonyl_chloride for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 16:14, 28 July 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,203 edits <ref name=eEROS> |
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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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| verifiedrevid = 449038116 |
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| Reference= |
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| verifiedrevid = 477223509 |
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|ImageFile1=P-Toluenesulfonyl chloride structure.svg |
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| ImageFile1=P-Toluenesulfonyl chloride structure.svg |
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|ImageSize1=150 |
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| ImageSize1=150 |
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|ImageFile2=Tosyl-chloride-3D-balls.png |
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|ImageSize2=150 |
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| ImageFile2=Tosyl-chloride-3D-vdW.png|ImageSize2=150 |
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|IUPACName= 4-methylbenzenesulfonyl chloride |
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| PIN= 4-Methylbenzene-1-sulfonyl chloride |
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|OtherNames= Tosyl chloride, p-toluenesulfonyl chloride, p-TsCl, TsCl |
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| OtherNames= Tosyl chloride, ''p''-toluenesulfonyl chloride, ''p''-TsCl, TsCl |
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|Section1= {{Chembox Identifiers |
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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 = 7119 |
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| ChemSpiderID = 7119 |
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| InChI = 1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3 |
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| InChI = 1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo= 98-59-9 |
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| CASNo= 98-59-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem= |
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| UNII = 027KYN78B4 |
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| SMILES = O=S(Cl)(=O)c1ccc(cc1)C |
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| PubChem=7397 |
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| SMILES = O=S(Cl)(=O)c1ccc(cc1)C |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>7</sub>H<sub>7</sub>ClO<sub>2</sub>S |
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| Formula=C<sub>7</sub>H<sub>7</sub>ClO<sub>2</sub>S |
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| MolarMass= 190.65 g/mol |
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| MolarMass= 190.65 g/mol |
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| Appearance=White solid |
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| Appearance=White solid |
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| Density= |
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| MeltingPtC = 65 to 69 |
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| MeltingPt=65-69 °C |
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| BoilingPt=134 °C at 10 mmHg |
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| BoilingPtC = 134 |
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| Solubility= hydrolysis |
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| BoilingPt_notes = at 10 mmHg |
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| Solubility= Reacts with water |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| reference = <ref>http://chemicalland21.com/specialtychem/finechem/p-TOLUENESULFONYL%20CHLORIDE.htm</ref> |
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| Hazards_ref = <ref>{{Cite web | url=http://chemicalland21.com/specialtychem/finechem/p-TOLUENESULFONYL%20CHLORIDE.htm | title=P-TOLUENESULFONYL CHLORIDE (TOSYL CHLORIDE)}}</ref> |
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| MainHazards= releases acid |
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| MainHazards= Releases ] on contact with water |
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| FlashPt=128 °C |
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| FlashPtC =128 |
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| NFPA-H = 3 |
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| NFPA-H = 3 |
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| NFPA-F = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-R = 0 |
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'''4-Toluenesulfonyl chloride''' ('''''p''-toluenesulfonyl chloride''', '''toluene-''p''-sulfonyl chloride''') is an ] with the formula CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>Cl. This white, malodorous solid is a ] widely used in ].<ref name=eEROS>{{ cite encyclopedia | author = Whitaker, D. T. | author2 = Whitaker, K. S. | author3 = Johnson, C. R. | author4 = Haas, J. | title = ''p''-Toluenesulfonyl Chloride | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | year = 2006 | publisher = John Wiley | location = New York | doi = 10.1002/047084289X.rt136.pub2 | chapter-url = http://onlinelibrary.wiley.com/o/eros/articles/rt136/frame.html | access-date = 2013-05-28 | archive-url = https://web.archive.org/web/20160305090729/http://onlinelibrary.wiley.com/o/eros/articles/rt136/frame.html | archive-date = 2016-03-05 | url-status = dead | chapter = P-Toluenesulfonyl Chloride | isbn = 978-0471936237 }}</ref> Abbreviated '''TsCl''' or '''TosCl''', it is a derivative of ] and contains a ] chloride (−SO<sub>2</sub>Cl) ]. |
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==Uses== |
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{{main|Tosyl}} |
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In characteristic manner, TsCl converts ]s (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"): |
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: CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>Cl + ROH → CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>OR + ] |
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Tosylates can be cleaved with lithium aluminium hydride: |
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: 4 CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>OR + LiAlH<sub>4</sub> → LiAl(O<sub>3</sub>SC<sub>6</sub>H<sub>4</sub>CH<sub>3</sub>)<sub>4</sub> + 4 RH |
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Thus, tosylation followed by reduction allows for removal of a hydroxyl group. |
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Likewise, TsCl is used to prepare ] from amines:<ref>{{OrgSynth | author = Ichikawa, J. | author2 = Nadano, R. | author3 = Mori, T. | author4 = Wada, Y. | title = 5-''endo''-''trig'' Cyclization of 1,1-Difluoro-1-alkenes: Synthesis of 3-Butyl-2-Fluoro-1-Tosylindole | year = 2006 | volume = 83 | pages = 111 | collvol = 11 | collvolpages = 834 | prep = v83p0111 }}</ref> |
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:CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>Cl + R<sub>2</sub>NH → CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>NR<sub>2</sub> + HCl |
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The resulting ]s are non-basic and, when derived from primary amines, are even acidic. |
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TsCl reacts with hydrazine to give ]. |
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The preparation of tosyl esters and amides are conducted in the presence of a base, which absorbs hydrogen chloride. The selection of the base is often crucial to the efficiency of tosylation. Typical bases include ] and ]. Unusual bases are also used; for example, catalytic amounts of trimethylammonium chloride in the presence of triethylamine is highly effective by virtue of the ].<ref name=eEROS/> |
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==Other reactions== |
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Being a widely available reagent, TsCl has been heavily examined from the perspective of reactivity. It is used in dehydrations to make ]s, ]s and ]s.<ref name=eEROS/> In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>Na.<ref>{{OrgSynth | author = Whitmore, F. C. | author2 = Hamilton, F. H. | title = Sodium Toluenesulfinate | year = 1922 | volume = 2 | pages = 89 | collvol = 1 | collvolpages = 492 | prep = CV1P0492 }}</ref> |
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==Manufacture== |
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This reagent is inexpensively available for laboratory use. It is a by-product from the production of ]-toluenesulfonyl chloride (a precursor for the synthesis of the common ] and catalyst ]), via the chlorosulfonation of ]:<ref>{{ Ullmann | author = Lindner, O. | author2 = Rodefeld, L. | title = Benzenesulfonic Acids and Their Derivatives | doi = 10.1002/14356007.a03_507 }}</ref> |
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: CH<sub>3</sub>C<sub>6</sub>H<sub>5</sub> + SO<sub>2</sub>Cl<sub>2</sub> → CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>Cl + HCl |
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== Hazards == |
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Tosyl chloride is "a corrosive ]."<ref name=eEROS/> |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Toluenesulfonyl chloride, 4-}} |
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] |
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] |
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] |
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] |