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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.
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.
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.
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]
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.
Chloral was first prepared, and named, by the German chemist Justus von Liebig in 1832. [2] Liebig treated anhydrous ethanol with dry chlorine gas. [3]Chloral is produced commercially by the chlorination of acetaldehyde in the presence of hydrochloric acid, producing chloral hydrate.
1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C 6 H 4 O 2.In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde.