“2,6-Dichlorophenol”的意思、由来-开放百科全书

词条

2,6-Dichlorophenol

释义

Preparation
References

{{Chembox
| Watchedfields = changed
| verifiedrevid = 477212051
| Reference = ^[1]
| ImageFileL1 = 2,6-dichlorophenol.svg
| ImageNameL1 = Skeletal formula
| ImageFileR1 = 2,6-Dichlorophenol-3D-balls.png
| ImageNameR1 = Ball-and-stick model
| PIN = 2,6-Dichlorophenol
| OtherNames =
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6633
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C07096
| InChI = 1/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H
| InChIKey = HOLHYSJJBXSLMV-UHFFFAOYAE
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 282597
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HOLHYSJJBXSLMV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 87-65-0
| PubChem = 6899
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28457
| EC_number = 201-761-3
| RTECS = SK8750000
| UNNumber = 2020 2021
| UNII = Q7E9K52W7E
| SMILES = Clc1cccc(Cl)c1O
}}
|Section2={{Chembox Properties
| C=6 | H=4 | Cl=2 | O=1
| Appearance = white solid
| Density =
| MeltingPtC = 64 to 66
| MeltingPt_notes =
| BoilingPtC = 218 to 220
| BoilingPt_notes =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|314|315|319|411}}
| 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}}
}}2,6-Dichlorophenol is a compound with formula C₆H₃Cl₂OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pK_a is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).^[2]

Preparation

It can be produced in a multistep process from phenol, 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.^[3]

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 decarboxylation affords 2,6-dichlorophenol.^[4]

References

1. ^2,6-Dichlorophenol at Sigma-Aldrich
2. ^{{Ullmann|authors=François Muller, Liliane Caillard|title=Chlorophenols|year=2011|doi=10.1002/14356007.a07_001.pub2}}
3. ^{{Ullmanns|authors=Otto Lindner, Lars Rodefeld|title=Benzenesulfonic Acids and Their Derivatives|year=2005|doi=10.1002/14356007.a03_507}}
4. ^{{cite journal|title=2,6-Dichlorophenol|authors=D. S. Tarbell, J. W. Wilson, Paul E. Fanta|journal=Org. Synth.|year=1949|volume=29|pages=35|doi=10.15227/orgsyn.029.0035}}

2 : Chloroarenes|Phenols

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