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Benzenehexol

Benzenehexol

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Encyclopedia
Benzenehexol, also called hexahydroxybenzene, is an organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with formula C6H6O6 or C6(OH)6. It is a six-fold alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

 of benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

. The product is also erroneously called hexaphenol, but this name has been used also for other substances.

Benzenehexol is a crystalline solid soluble in hot water, with melting point higher than 310°. It can be prepared from inositol
Inositol
Inositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula 6126 or 6, a sixfold alcohol of cyclohexane. It exists in nine possible stereoisomers, of which the most prominent form, widely occurring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol...

 (cyclohexanehexol). Oxidation of benzenehexol yields tetrahydroxy-p-benzoquinone (THBQ), rhodizonic acid
Rhodizonic acid
Rhodizonic acid is a chemical compound with formula C6H2O6 or 42. It can be seen as a two-fold alcohol and four-fold ketone of cyclohexene, more precisely 5,6-dihydroxycyclohex-5-ene-1,2,3,4-tetrone....

, and dodecahydroxycyclohexane
Dodecahydroxycyclohexane
Dodecahydroxycyclohexane is an organic compound with molecular formula C6O12H12 or C612. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone .-Dihydrate:...

. Conversely, benzenehexol can be obtained by reduction of sodium
Sodium
Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...

 THBQ salt with SnCl2
Tin(II) chloride
Tin chloride is a white crystalline solid with the formula 2. It forms a stable dihydrate, but aqueous solutions tend to undergo hydrolysis, particularly if hot. SnCl2 is widely used as a reducing agent , and in electrolytic baths for tin-plating...

/HCl
Hydrogen chloride
The compound hydrogen chloride has the formula HCl. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity. Hydrogen chloride gas and hydrochloric acid are important in technology and industry...

.

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

Benzenehexol forms an adduct
Adduct
An adduct 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 considered a distinct molecular species...

 with 2,2'-bipyridine
2,2'-Bipyridine
2,2'-Bipyridine is a organic compound with the formula . This colorless solid, commonly abbreviated bipy or bpy , is an important isomer of the bipyridine family. It is a bidentate chelating ligand, forming complexes with many transition metals...

, with 1:2 molecular ratio.

Benzenehexolate


Like most phenols, benzenehexol can lose the six H+
Proton
The proton is a subatomic particle with the symbol or and a positive electric charge of 1 elementary charge. One or more protons are present in the nucleus of each atom, along with neutrons. The number of protons in each atom is its atomic number....

 ions from the hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...

 groups yielding the hexaanion C6O66−. The potassium
Potassium
Potassium is the chemical element with the symbol K and atomic number 19. Elemental potassium is a soft silvery-white alkali metal that oxidizes rapidly in air and is very reactive with water, generating sufficient heat to ignite the hydrogen emitted in the reaction.Potassium and sodium are...

 salt of this anion is one of the components of Liebig
Justus von Liebig
Justus von Liebig was a German chemist who made major contributions to agricultural and biological chemistry, and worked on the organization of organic chemistry. As a professor, he devised the modern laboratory-oriented teaching method, and for such innovations, he is regarded as one of the...

's so-called "potassium carbonyl", the product of the reaction of carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...

 with potassium. The hexaanion is produced by trimerization of the acetylenediolate anion when heating potassium acetylenediolate . The nature of was clarified by B. Nietzki and T. Benckiser in 1885, who found that its hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

 yielded benzenehexol.

The lithium
Lithium
Lithium is a soft, silver-white metal that belongs to the alkali metal group of chemical elements. It is represented by the symbol Li, and it has the atomic number 3. Under standard conditions it is the lightest metal and the least dense solid element. Like all alkali metals, lithium is highly...

 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).