2,6-Dichlorophenol: Difference between revisions

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	\| C=6 \| H=4 \| Cl=2 \| O=1		\| C=6 \| H=4 \| Cl=2 \| O=1
	\| Appearance = white solid		\| Appearance = white solid
	\| Density =		\| Density = 1.653 g/cm<sup>3</sup> at 20 °C<ref name=crc/>
	\| MeltingPtC = ~~64 to~~ 66		\| MeltingPtC = 66.6
			\| MeltingPt_ref=<ref name=crc>Haynes, p. 3.166</ref>
	\| MeltingPt_notes =
	\| BoilingPtC = ~~218 to 220~~		\| BoilingPtC = 226
			\| BoilingPt_ref = <ref name=crc/>
	\| BoilingPt_notes =
	\| Solubility = }}		\| Solubility = }}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
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	==References==		==References==
	{{reflist}}		{{reflist}}
			==Cited sources==
			*{{cite book \|ref=Haynes\| editor= Haynes, William M. \| date = 2016\| title = ] \| edition = 97th \| publisher = ] \| isbn = 9781498754293}}

	{{DEFAULTSORT:Dichlorophenol, 2,6-}}		{{DEFAULTSORT:Dichlorophenol, 2,6-}}

Latest revision as of 00:44, 28 June 2023

2,6-Dichlorophenol

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/h1-3,9HKey: HOLHYSJJBXSLMV-UHFFFAOYSA-N
InChI=1/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9HKey: HOLHYSJJBXSLMV-UHFFFAOYAE

SMILES

Clc1cccc(Cl)c1O

Properties

Chemical formula

C₆H₄Cl₂O

Molar mass

163.00 g·mol

Appearance

white solid

Density

1.653 g/cm 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 , 100 kPa).

Y verify (what is ?) Infobox references

Chemical compound

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).

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.

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.

References

2,6-Dichlorophenol at Sigma-Aldrich
^ 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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