Benzenehexol, also called hexahydroxybenzene, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with formula or . It is a six-fold

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

. 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 In biochemistry, medicine, and related sciences, inositol generally refers to ''myo''-inositol (formerly ''meso''-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its elemental formula, formula is ...

(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 dihydr ...

, and

dodecahydroxycyclohexane Dodecahydroxycyclohexane is an 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 can be crystallize ...

. Conversely, benzenehexol can be obtained by reduction of

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

THBQ salt with SnCl₂/

HCl HCL may refer to: Science and medicine * Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia * Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development * Hollow-cathode lamp, a s ...

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

adduct In chemistry, an adduct (; 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 components. The resultant is ...

with

2,2'-bipyridine The comma is a punctuation mark that appears in several variants in different languages. Some typefaces render it as a small line, slightly curved or straight, but inclined from the vertical; others give it the appearance of a miniature fille ...

, 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 hydroxy ...

groups, yielding the hexaanion . The

potassium Potassium is a chemical element; it has Symbol (chemistry), symbol K (from Neo-Latin ) and atomic number19. It is a silvery white metal that is soft enough to easily cut with a knife. Potassium metal reacts rapidly with atmospheric oxygen to ...

salt of this anion is one of the components of

Liebig Justus ''Freiherr'' von Liebig (12 May 1803 – 18 April 1873) was a Germans, German scientist who made major contributions to the theory, practice, and pedagogy of chemistry, as well as to agricultural and biology, biological chemistry; he is ...

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

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

with potassium. The hexaanion is produced by trimerization of the acetylenediolate anion when heating potassium acetylenediolate . The nature of was clarified by

Rudolf Nietzki Rudolf Hugo Nietzki (9 March 1847 – 28 September 1917) was a German chemist who specialized in industrial dyes derived from coal tar. While a professor at the University of Basel in Switzerland he initiated the university's association with to t ...

and 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 reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

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 Lithium (from , , ) is a chemical element; it has chemical symbol, symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard temperature and pressure, standard conditions, it is the least dense metal and the ...

salt of this anion, Li₆C₆O₆ has been considered for

electric battery An electric battery is a source of electric power consisting of one or more electrochemical cells with external connections for powering electrical devices. When a battery is supplying power, its positive Terminal (electronics), terminal is the ...

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 Polyphenols