Benzenehexol
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Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula Template:Chem/link or Template:Chem/link. It is a six-fold phenol of benzene.[2][3] The product is also called hexaphenol,[4] but this name has been used also for other substances.[5]
Benzenehexol is a crystalline solid soluble in hot water,[4] with a melting point above 310°.[2] It can be prepared from inositol (cyclohexanehexol).Script error: No such module "Unsubst". Oxidation of benzenehexol yields tetrahydroxy-p-benzoquinone (THBQ), rhodizonic acid, and dodecahydroxycyclohexane.[6] Conversely, benzenehexol can be obtained by reduction of sodium THBQ salt with SnCl2/HCl.[7]
Benzenehexol is a starting material for a class of discotic liquid crystals.[7]
Benzenehexol forms an adduct with 2,2'-bipyridine, with 1:2 molecular ratio.[8]
Benzenehexolate
Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanion Template:Chem/link. The potassium salt of this anion is one of the components of Liebig's so-called "potassium carbonyl", the product of the reaction of carbon monoxide with potassium. The hexaanion is produced by trimerization of the acetylenediolate anion Template:Chem/link when heating potassium acetylenediolate Template:Chem/link.[9] The nature of Template:Chem/link was clarified[10] by Rudolf Nietzki and Template:Ill in 1885, who found that its hydrolysis yielded benzenehexol.[11][12]
The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications.[13]
Esters
Hexahydroxy benzene forms esters such as the hexaacetate Template:Chem/link(-O(CO)CH3)6 (melting point 220 °C) and ethers like hexa-tert-butoxybenzene Template:Chem/link(-OC(CH3)3)6 (melting point 223 °C).[9]
References
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- ↑ Ludwig Mond (1892), On metallic carbonyls. Proceedings of the Royal Institution, volume 13, pages 668-680. Reprinted in The Development of Chemistry, 1789-1914: Selected essays edited by D. Knight (1998). Template:ISBN Online version at books.google.com, accessed on 2010-01-15.
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