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Benzenehexol

Hexahydroxybenzene 2,3,4,5,6-pentahydroxyphenol 1,2,3,4,5,6-hexahydroxybenzene Hexaphenol Fenolão

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula or . It is a six-fold phenol of benzene. The product is also called hexaphenol, but this name has been used also for other substances.

Benzenehexol is a crystalline solid soluble in hot water, with a melting point above 310°. It can be prepared from inositol (cyclohexanehexol). Oxidation of benzenehexol yields tetrahydroxy-p-benzoquinone (THBQ), rhodizonic acid, and dodecahydroxycyclohexane. Conversely, benzenehexol can be obtained by reduction of sodium THBQ salt with SnCl2/HCl.

Benzenehexol is a starting material for a class of discotic liquid crystals.

Benzenehexol forms an adduct with 2,2'-bipyridine, with 1:2 molecular ratio.

Benzenehexolate

Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanion . 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 when heating potassium acetylenediolate . The nature of was clarified by Rudolf Nietzki and in 1885, who found that its hydrolysis yielded benzenehexol. 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). Online version at books.google.com, accessed on 2010-01-15.

The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications.

Esters

Hexahydroxy benzene forms esters such as the hexaacetate (-O(CO)CH3)6 (melting point 220 °C) and ethers like hexa-tert-butoxybenzene (-OC(CH3)3)6 (melting point 223 °C).

References

(2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
"Hexahydroxybenzene (Benzenehexol)".
Leston, Gerd. (2000-12-04). "(Polyhydroxy)benzenes". John Wiley & Sons, Inc..
(1996). "Dictionary of Organic Compounds, 6th edition". Chapman & Hall; CRC Press.
"Hexaphenol (CAS: 1506-76-9)".
(March–April 1963). "Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)". Journal of Research of the National Bureau of Standards Section A.
Kumar, Sandeep. (2006). "Self-organization of disc-like molecules: chemical aspects". Chemical Society Reviews.
Cowan John A., Howard Judith A. K., Leech Michael A., Puschmann Horst, Williams Ian D.. (2001). "''Hexahydroxybenzene—2,2'-bipyridine (1/2)''". Acta Crystallographica Section C.
Serratosa Fèlix. (1983). "Acetylene Diethers: A Logical Entry to Oxocarbons". Acc. Chem. Res..
{{Cite Q. Q56853054
Büchner Werner, Weiss E. (1964). "Zur Kenntnis der sogenannten "Alkalicarbonyle" IV[1] Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid". Helvetica Chimica Acta.
Chen Haiyan, Armand Michel, Courty Matthieu, Jiang Meng, Grey Clare P., Dolhem Franck, Tarascon Jean-Marie, Poizot Philippe. (2009). "Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery". J. Am. Chem. Soc..

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