2,6-Dichlorophenol

2,6-Dichlorophenol[1]
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
2,6-Dichlorophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.602 Edit this at Wikidata
EC Number
  • 201-761-3
KEGG
RTECS number
  • SK8750000
UNII
UN number 2020 2021
  • InChI=1S/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H checkY
    Key: HOLHYSJJBXSLMV-UHFFFAOYSA-N checkY
  • InChI=1/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H
    Key: HOLHYSJJBXSLMV-UHFFFAOYAE
  • Clc1cccc(Cl)c1O
Properties
C6H4Cl2O
Molar mass 163.00 g·mol−1
Appearance white solid
Density 1.653 g/cm3 at 20 °C[2]
Melting point 66.6 °C (151.9 °F; 339.8 K)[2]
Boiling point 226 °C (439 °F; 499 K)[2]
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H314, H315, H319, H411
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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).[3]

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.[4]

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.[5]

References

  1. ^ 2,6-Dichlorophenol at Sigma-Aldrich
  2. ^ a b c 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


Stub icon

This article about an organic halide is a stub. You can help Wikipedia by expanding it.