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)
|
|
ChemSpider | |
ECHA InfoCard | 100.204.877 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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). 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]
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 by
R. Nietzki and
T. Benckiser in 1885, who found that its
hydrolysis yielded benzenehexol.
[10]
[11]
[12]
The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications. [13]
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]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
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)
|
|
ChemSpider | |
ECHA InfoCard | 100.204.877 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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). 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]
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 by
R. Nietzki and
T. Benckiser in 1885, who found that its
hydrolysis yielded benzenehexol.
[10]
[11]
[12]
The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications. [13]
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]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)