4-Chlorophenol is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula C₆H₄ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pK_a is 9.41.

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. It once was produced on a large scale as a precursor to

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para' ...

. It is a classic precursor, upon reaction with

phthalic anhydride Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commer ...

, to quinizarin. The commercial dye quinizarin is produced by the reaction of

and 4-chlorophenol followed by hydrolysis of the chloride. left, Clofibrate, a drug for controlling the high cholesterol and triacylglyceride level in the blood, is derived from 4-chlorophenol.

References

Cited sources

* {{DEFAULTSORT:Chlorophenol, 4- 4-Chlorophenyl compounds 4-Hydroxyphenyl compounds