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
Density	1.653 g/cm3 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
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 [77 °F], 100 kPa). verify (what is ?) 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).^[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

^ 2,6-Dichlorophenol at Sigma-Aldrich
^ ^a ^b ^c Haynes, p. 3.166
^ 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.
^ 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.
^ 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

Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

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[1] 2,6-Dichlorophenol at Sigma-Aldrich

[crc-2] Haynes, p. 3.166

[Ullmann-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.

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