Benzenehexol

Benzenehexol

Names
Preferred IUPAC name Benzenehexol
Other names Benzene-1,2,3,4,5,6-hexol Hexahydroxybenzene 2,3,4,5,6-pentahydroxyphenol 1,2,3,4,5,6-hexahydroxybenzene
Identifiers
CAS Number	608-80-0 Y
3D model (Jmol)	Interactive image
ChemSpider	62319 Y
ECHA InfoCard	100.204.877
PubChem CID	69102
InChI InChI=1S/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H Y Key: VWPUAXALDFFXJW-UHFFFAOYSA-N Y InChI=1/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H Key: VWPUAXALDFFXJW-UHFFFAOYAU
SMILES c1(c(c(c(c(c1O)O)O)O)O)O
Properties
Chemical formula	C6H6O6
Molar mass	174.11
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C₆H₆O₆ or C₆(OH)₆. 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.

Like most phenols, benzenehexol can lose the six H⁺ ions from the hydroxyl groups, yielding the hexaanion C₆O₆⁶⁻. 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. The nature of K
6C
6O
6 was clarified by R. Nietzki and T. Benckiser in 1885, who found that its hydrolysis yielded benzenehexol.