2,6-Dichlorophenol

2,6-Dichlorophenol[1]
Skeletal formula	Ball-and-stick model
Names
	Preferred IUPAC name 2,6-Dichlorophenol
Identifiers
CAS Number	87-65-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28457 ;
ChEMBL	ChEMBL282597 ;
ChemSpider	6633 ;
ECHA InfoCard	100.001.602
EC Number	201-761-3;
KEGG	C07096 ;
PubChem CID	6899;
RTECS number	SK8750000;
UNII	Q7E9K52W7E;
UN number	2020 2021
CompTox Dashboard (EPA)	DTXSID2025004 ;
	InChI InChI=1S/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H Key: HOLHYSJJBXSLMV-UHFFFAOYSA-N ; InChI=1/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H Key: HOLHYSJJBXSLMV-UHFFFAOYAE;
	SMILES Clc1cccc(Cl)c1O;
Properties
Chemical formula	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
GHS hazard statements	H314, H315, H319, H411
GHS precautionary statements	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

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

2,6-Dichlorophenol at Sigma-Aldrich
François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
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.
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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[1] 2,6-Dichlorophenol at Sigma-Aldrich

[Ullmann-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.