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Chloranil is a quinone with the molecular formula C 6 Cl 4 O 2. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Like the parent benzoquinone, chloranil is a planar molecule [ 2 ] that functions as a mild oxidant.
Chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) is an organic compound mainly used as a broad spectrum, nonsystemic fungicide, with other uses as a wood protectant, pesticide, acaricide, and to control mold, mildew, bacteria, algae. [2]
Synthesis of DDQ involves cyanation of chloranil. J. Thiele and F. Günther first reported a 6-step preparation in 1906. [7] The substance did not receive interest until its potential as a dehydrogenation agent was discovered. A single-step chlorination from 2,3-dicyanohydroquinone was reported in 1965. [8]
Relative to benzoquinone, more strongly oxidizing quinones include chloranil and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (also known as DDQ). [6] The oxidizing power of quinones is enhanced by the presence of acids. [7] In acidic conditions, quinone undergoes two-electron and two-proton reduction to hydroquinone.
It is a red-orange solid. The compound is obtained by hydrolysis of chloranil: C 6 Cl 4 O 2 + 2 H 2 O → C 6 Cl 2 O 2 (OH) 2 + 2 HCl. It is centrosymmetric, planar molecule. It also crystallizes as a dihydrate. [2] Chloranilic acid is a noteworthy hydroxyquinone that is somewhat acidic owing to the presence of the two chloride substituents.
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Many organochlorine compounds have been isolated from natural sources ranging from bacteria to humans. [3] [4] Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids.