Benzenehexol
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 Edit this at Wikidata
UNII
  • InChI=1S/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H checkY
    Key: VWPUAXALDFFXJW-UHFFFAOYSA-N checkY
  • 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).
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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]

Benzenehexolate

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]

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]

References

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 693. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b 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)
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