| Revision as of 17:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443313796 of page 2,6-Dichlorophenol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 00:44, 28 June 2023 edit Materialscientist (talk | contribs)Edit filter managers, Autopatrolled, Checkusers, Administrators1,993,751 edits add |
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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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| Watchedfields = changed |
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| verifiedrevid = 443312855 |
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| verifiedrevid = 477212051 |
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| Reference = <ref> at ]</ref> |
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| Reference = <ref> at ]</ref> |
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| ImageFileL1 = 2,6-dichlorophenol.svg |
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| ImageFileL1 = 2,6-dichlorophenol.svg |
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| ImageSizeL1 = 120px |
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| ImageNameL1 = Skeletal formula |
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| ImageNameL1 = Skeletal formula |
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| ImageFileR1 = 2,6-Dichlorophenol-3D-balls.png |
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| ImageFileR1 = 2,6-Dichlorophenol-3D-balls.png |
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| ImageSizeR1 = 120px |
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| ImageNameR1 = Ball-and-stick model |
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| ImageNameR1 = Ball-and-stick model |
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| IUPACName = 2,6-Dichlorophenol |
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| PIN = 2,6-Dichlorophenol |
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| OtherNames = |
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| OtherNames = |
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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 = 6633 |
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| ChemSpiderID = 6633 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 87-65-0 |
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| CASNo = 87-65-0 |
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| PubChem = |
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| PubChem = 6899 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28457 |
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| ChEBI = 28457 |
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| EC_number = 201-761-3 |
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| RTECS = SK8750000 |
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| UNNumber = 2020 2021 |
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| UNII = Q7E9K52W7E |
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| SMILES = Clc1cccc(Cl)c1O |
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| SMILES = Clc1cccc(Cl)c1O |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6 | H = 4 | Cl = 2 | O =1 |
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| C=6 | H=4 | Cl=2 | O=1 |
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| Appearance = |
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| Appearance = white solid |
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| Density = |
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| Density = 1.653 g/cm<sup>3</sup> at 20 °C<ref name=crc/> |
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| MeltingPt = 64-66 °C |
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| MeltingPtC = 66.6 |
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| MeltingPt_ref=<ref name=crc>Haynes, p. 3.166</ref> |
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| BoilingPt = 218-220 °C |
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| BoilingPtC = 226 |
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| BoilingPt_ref = <ref name=crc/> |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = |
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| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|314|315|319|411}} |
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| PPhrases = {{P-phrases|260|264|273|280|301+330+331|302+352|303+361+353|304+340|305+351+338|310|321|332+313|337+313|362|363|391|405|501}} |
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'''2,6-Dichlorophenol''' is a ] with formula C<sub>6</sub>H<sub>3</sub>Cl<sub>2</sub>OH. It is one of the six ]s of ]. It is a colorless solid. Its pK<sub>a</sub> is 6.78, which is about 100x more acidic than ] (8.52) and 1000x more acidic than phenol itself (9.95).<ref name=Ullmann>{{Ullmann|author1=François Muller |author2=Liliane Caillard|title=Chlorophenols|year=2011|doi=10.1002/14356007.a07_001.pub2}}</ref> |
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==Preparation== |
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It can be produced in a multistep process from ], which is converted to its 4-sulfonic acid derivative. The resulting phenol sulfonic acid chlorinates at the positions flanking the phenol. Hydrolysis releases the sulfonic acid group.<ref>{{Ullmanns|author1=Otto Lindner |author2=Lars Rodefeld|title=Benzenesulfonic Acids and Their Derivatives|year=2005|doi=10.1002/14356007.a03_507}}</ref> |
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An alternative synthesis starts with the ethyl ester of 4-hydroxybenzoic acid, which chlorinates at the positions flanking the phenolic center. Ester hydrolysis followed by ] affords 2,6-dichlorophenol.<ref>{{cite journal|title=2,6-Dichlorophenol|author1=D. S. Tarbell |author2=J. W. Wilson |author3=Paul E. Fanta|journal=Org. Synth.|year=1949|volume=29|pages=35|doi=10.15227/orgsyn.029.0035}}</ref> |
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==References== |
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{{reflist}} |
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==Cited sources== |
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*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}} |
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{{DEFAULTSORT:Dichlorophenol, 2,6-}} |
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] |
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] |
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{{organohalide-stub}} |