Benzenehexol, also called hexahydroxybenzene, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

with formula or . It is a six-fold

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

. 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 Rhodizonic acid is a chemical compound with formula or . It can be seen as a twofold enol and fourfold ketone of cyclohexene, more precisely 5,6-dihydroxycyclohex-5-ene-1,2,3,4-tetrone. Rhodizonic acid is usually obtained in the form of a dihyd ...

, and

dodecahydroxycyclohexane Dodecahydroxycyclohexane is an organic chemistry, organic compound with molecular formula or or . It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone (). Dihydrate The dihydrate ...

. Conversely, benzenehexol can be obtained by reduction of

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...

THBQ salt with SnCl₂/ HCl. Benzenehexol is a starting material for a class of discotic liquid crystals. Benzenehexol forms an

adduct An adduct (from the Latin ''adductus'', "drawn toward" alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all co ...

with

2,2'-bipyridine The comma is a punctuation mark that appears in several variants in different languages. It has the same shape as an apostrophe or single closing quotation mark () in many typefaces, but it differs from them in being placed on the baseline ...

, with 1:2 molecular ratio.

Benzenehexolate

Like most phenols, benzenehexol can lose the six H⁺ ions from the

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydro ...

groups, yielding the hexaanion . The

potassium Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosph ...

salt of this anion is one of the components of

Liebig Justus Freiherr von Liebig (12 May 1803 – 20 April 1873) was a German scientist who made major contributions to agricultural and biological chemistry, and is considered one of the principal founders of organic chemistry. As a professor at t ...

's so-called "potassium carbonyl", the product of the reaction of

carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...

with potassium. The hexaanion is produced by trimerization of the

acetylenediolate Acetylenediol, or ethynediol, is a chemical substance with formula HO−C≡C−OH (an ynol). It is the diol of acetylene. Acetylenediol is unstable in the condensed phase, although its tautomer glyoxal (CHO)2 is well known. Detection Acetyle ...

anion when heating potassium acetylenediolate . The nature of was clarified by R. Nietzki and T. Benckiser in 1885, who found that its

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolys ...

yielded benzenehexol. R. Nietzki and T. Benckiser (1885), Berichte Chemie, volume 18, page 1834. Cited by Fatiadi and Sanger. 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 Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid ...

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

{{reflist Phenols