4-Chlorophenol
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Names | |
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Preferred IUPAC name
4-Chlorophenol | |
Other names
p-Chlorophenol
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Identifiers | |
3D model (JSmol)
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3DMet | |
507004 | |
ChEBI | |
ChEMBL | |
ECHA InfoCard | 100.003.094 ![]() |
EC Number |
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2902 | |
KEGG | |
PubChem CID
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RTECS number |
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UNII | |
UN number | 2020 |
CompTox Dashboard (EPA)
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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 | |
Refractive index (nD)
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1.5579 |
Hazards | |
GHS labelling: | |
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Signal word
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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 | |
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.
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]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Clofibrate.svg/220px-Clofibrate.svg.png)
Clofibrate, a drug for controlling the high cholesterol and triacylglyceride level in the blood, is derived from 4-chlorophenol.
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References[]
- ^ a b François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
- ^ Bigelow, L. A.; Reynolds, H. H. (1926). "Quinizarin". Org. Synth. 6: 78. doi:10.15227/orgsyn.006.0078.
- ^ 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.
Categories:
- Chloroarenes
- Phenols