Benzenehexol
| Names | |
|---|---|
| Preferred IUPAC name
Benzenehexol[1] | |
| Other names
Benzene-1,2,3,4,5,6-hexol
Hexahydroxybenzene 2,3,4,5,6-pentahydroxyphenol 1,2,3,4,5,6-hexahydroxybenzene Hexaphenol Fenolão | |
| Identifiers | |
3D model (JSmol)
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H6O6 | |
| Molar mass | 174.108 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C
6H
6O
6 or C
6(OH)
6. 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).[citation needed] 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
[edit | edit source]Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanion C
6O6−
6. 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 C
2O2−
2 when heating potassium acetylenediolate K
2C
2O
2.[9] The nature of K
6C
6O
6 was clarified[10] by Rudolf Nietzki and Theodor Benckiser 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
[edit | edit source]Hexahydroxy benzene forms esters such as the hexaacetate C
6(-O(CO)CH3)6 (melting point 220 °C) and ethers like hexa-tert-butoxybenzene C
6(-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). Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Online version at books.google.com, accessed on 2010-01-15.
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