Benzenehexol

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Benzenehexol
Benzenehexol.svg
Hexahydroxybenzene-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H Yes check.svgY
    Key: VWPUAXALDFFXJW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H
    Key: VWPUAXALDFFXJW-UHFFFAOYAU
  • c1(c(c(c(c(c1O)O)O)O)O)O
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C
6
H
6
O
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]

Contents

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]

Benzenehexolate

Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanion C
6
O6−
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
2
O2−
2
when heating potassium acetylenediolate K
2
C
2
O
2
. [9] The nature of K
6
C
6
O
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]

Esters

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]

Related Research Articles

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In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

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<span class="mw-page-title-main">Polyoxometalate</span> Polyatomic ion made of ≥3 transition metal oxyanions bound by oxygen in a 3D structure

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Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone, is an organic compound with formula C6O2(OH)4. Its molecular structure consists of a cyclohexadiene ring with four hydroxyl groups and two ketone groups in opposite (para) positions.

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Croconate blue or 1,2,3-tris(dicyanomethylene)croconate is a divalent anion with chemical formula C
14
N
6
O2−
2
or ((N≡C−)2C=)3(C5O2)2−. It is one of the pseudo-oxocarbon anions, as it can be described as a derivative of the croconate oxocarbon anion C
5
O2−
5
through the replacement of three oxygen atoms by dicyanomethylene groups =C(−C≡N)2. The term Croconate Blue as a dye name specifically refers to the dipotassium salt K
2
C
14
N
6
O
2
.

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References

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  2. 1 2 Fatiadi, Alexander J.; Sager, William F. "Hexahydroxybenzene (Benzenehexol)". Organic Syntheses. Retrieved 2023-01-28.
  3. Leston, Gerd (2000-12-04), "(Polyhydroxy)benzenes", in John Wiley & Sons, Inc. (ed.), Kirk-Othmer Encyclopedia of Chemical Technology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 1615122512051920.a01, doi:10.1002/0471238961.1615122512051920.a01, ISBN   978-0-471-23896-6 , retrieved 2023-01-28
  4. 1 2 Codagan, J.I.G.; Buckingham, John; MacDonald, Finlay J.; Rhodes, P. H. (1996). Dictionary of Organic Compounds, 6th edition. London: Chapman & Hall; CRC Press. ISBN   9780412540905. OCLC   35716592.
  5. "Hexaphenol (CAS: 1506-76-9)". www.chemicalbook.com. Retrieved 2009-07-05.
  6. Fatiadi, Alexander J.; Isbell, Horace S.; Sager, William F. (March–April 1963). "Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)" (PDF). Journal of Research of the National Bureau of Standards Section A. 67A (2): 153–162. doi:10.6028/jres.067A.015. PMC   6640573 . PMID   31580622. Archived from the original (PDF) on 2009-03-25. Retrieved 2009-07-05.
  7. 1 2 Kumar, Sandeep (2006). "Self-organization of disc-like molecules: chemical aspects". Chemical Society Reviews. 35 (1): 83–109. doi:10.1039/b506619k. PMID   16365644.
  8. Cowan John A., Howard Judith A. K., Leech Michael A., Puschmann Horst, Williams Ian D. (2001). "Hexahydroxybenzene—2,2'-bipyridine (1/2)". Acta Crystallographica Section C. 57 (10): 1194–1195. doi:10.1107/S0108270101011350. PMID   11600782. S2CID   25797464.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. 1 2 Serratosa Fèlix (1983). "Acetylene Diethers: A Logical Entry to Oxocarbons". Acc. Chem. Res. 16 (5): 170–176. doi:10.1021/ar00089a004.
  10. R. Nietzki and T. Benckiser (1885), Berichte Chemie, volume 18, page 1834. Cited by Fatiadi and Sanger.
  11. 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). ISBN   0-415-17912-2 Online version at books.google.com, accessed on 2010-01-15.
  12. Büchner Werner, Weiss E (1964). "Zur Kenntnis der sogenannten "Alkalicarbonyle" IV[1] Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid". Helvetica Chimica Acta. 47 (6): 1415–1423. doi:10.1002/hlca.19640470604.
  13. Chen Haiyan, Armand Michel, Courty Matthieu, Jiang Meng, Grey Clare P., Dolhem Franck, Tarascon Jean-Marie, Poizot Philippe (2009). "Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery". J. Am. Chem. Soc. 131 (25): 8984–8988. doi:10.1021/ja9024897. PMID   19476355.{{cite journal}}: CS1 maint: multiple names: authors list (link)