2,6-Dichlorophenol

2,6-Dichlorophenol^[1]
Skeletal formulaSkeletal formula	Ball-and-stick modelBall-and-stick model
Names
	Preferred IUPAC name 2,6-Dichlorophenol
Identifiers
CAS Number	87-65-0 check;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28457 check;
ChEMBL	ChEMBL282597 check;
ChemSpider	6633 check;
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number	201-761-3;
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG	C07096 check;
PubChem CID	6899;
RTECS number	SK8750000;
UNII	Q7E9K52W7E;
UN number	2020 2021
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
	InChI InChI=1S/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H check Key: HOLHYSJJBXSLMV-UHFFFAOYSA-N check; 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	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 [77 °F], 100 kPa). check verify (what is check☒ ?) 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
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Cited sources

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

[crc-2] Haynes, p. 3.166

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2,6-Dichlorophenol

Preparation

References

Cited sources

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