2,6-Dichlorophenol

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).[2]

2,6-Dichlorophenol[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2,6-Dichlorophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.602
EC Number
  • 201-761-3
KEGG
RTECS number
  • SK8750000
UNII
UN number 2020 2021
Properties
C6H4Cl2O
Molar mass 163.00 g·mol−1
Appearance white solid
Melting point 64 to 66 °C (147 to 151 °F; 337 to 339 K)
Boiling point 218 to 220 °C (424 to 428 °F; 491 to 493 K)
Hazards
GHS pictograms
GHS Signal word Danger
H314, H315, H319, H411
P260, P264, P273, P280, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P321, P332+313, P337+313, P362, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
  3. 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.
  4. D. S. Tarbell; J. W. Wilson; Paul E. Fanta (1949). "2,6-Dichlorophenol". Org. Synth. 29: 35. doi:10.15227/orgsyn.029.0035.


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