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2,6-Dichlorophenol

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2,6-Dichlorophenol
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name 2,6-Dichlorophenol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.602 Edit this at Wikidata
EC Number
  • 201-761-3
KEGG
PubChem CID
RTECS number
  • SK8750000
UNII
UN number 2020 2021
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9HKey: HOLHYSJJBXSLMV-UHFFFAOYSA-N
  • InChI=1/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9HKey: HOLHYSJJBXSLMV-UHFFFAOYAE
SMILES
  • Clc1cccc(Cl)c1O
Properties
Chemical formula C6H4Cl2O
Molar mass 163.00 g·mol
Appearance white solid
Density 1.653 g/cm at 20 °C
Melting point 66.6 °C (151.9 °F; 339.8 K)
Boiling point 226 °C (439 °F; 499 K)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Signal word Danger
Hazard statements H314, H315, H319, H411
Precautionary statements P260, P264, P273, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P332+P313, P337+P313, P362, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).

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.

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.

References

  1. 2,6-Dichlorophenol at Sigma-Aldrich
  2. ^ Haynes, p. 3.166
  3. François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3527306732.
  4. Otto Lindner; Lars Rodefeld (2005). "Benzenesulfonic Acids and Their Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_507. ISBN 978-3527306732.
  5. D. S. Tarbell; J. W. Wilson; Paul E. Fanta (1949). "2,6-Dichlorophenol". Org. Synth. 29: 35. doi:10.15227/orgsyn.029.0035.

Cited sources


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