4-Chlorophenol

4-Chlorophenol is an organic compound with the formula ClC6H4OH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.

4-Chlorophenol
Names
Preferred IUPAC name
4-Chlorophenol
Other names
p-Chlorophenol
Identifiers
3D model (JSmol)
3DMet
507004
ChEBI
ChEMBL
ECHA InfoCard 100.003.094
EC Number
  • 203-402-6
2902
KEGG
RTECS number
  • SK2800000
UNII
UN number 2020
  • InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H
    Key: WXNZTHHGJRFXKQ-UHFFFAOYSA-N
  • C1=CC(=CC=C1O)Cl
Properties
C6H5ClO
Molar mass 128.56 g·mol−1
Appearance White solid
Density 1.31 g/cm3
Melting point 42.8 °C (109.0 °F; 315.9 K)
Boiling point 217 °C (423 °F; 490 K)
27.1 g/L
1.5579
Hazards
GHS labelling:
Danger
H290, H301, H302, H312, H314, H332, H411
P234, P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P390, P391, P404, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation and reaction

It is prepared by chlorination of phenol, preferably in polar solvents, which tends to yield the 4-chloro derivative. Direct chlorination of molten phenol favors the formation of 2-chlorophenol.[1]

It once was produced on a large scale as a precursor to hydroquinone.[1] It is a classic precursor, upon reaction with phthalic anhydride, to quinizarin.[2] The commercial dye quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride.[3]

Clofibrate, a drug for controlling the high cholesterol and triacylglyceride level in the blood, is derived from 4-chlorophenol.

References
  1. François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
  2. Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.
  3. Bien, H.-S.; Stawitz, J.; Wunderlich, K. "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355.
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