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
608-80-0 YesY
3D model (Jmol) Interactive image
ChemSpider 62319 YesY
ECHA InfoCard 100.204.877
PubChem 69102
Properties
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).
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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.[1][2] The product is also called hexaphenol,[3] but this name has been used also for other substances.[4]

Benzenehexol is a crystalline solid soluble in hot water,[3] with a melting point above 310°.[1] It can be prepared from inositol (cyclohexanehexol). Oxidation of benzenehexol yields tetrahydroxy-p-benzoquinone (THBQ), rhodizonic acid, and dodecahydroxycyclohexane.[5] Conversely, benzenehexol can be obtained by reduction of sodium THBQ salt with SnCl2/HCl.[6]

Benzenehexol is a starting material for a class of discotic liquid crystals.[6]

Benzenehexol forms an adduct with 2,2'-bipyridine, with 1:2 molecular ratio.[7]

Benzenehexolate

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.[8] The nature of K
6C
6O
6 was clarified by R. Nietzki and T. Benckiser in 1885, who found that its hydrolysis yielded benzenehexol.[9][10][11]

The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications.[12]

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).[8]

References

  1. 1 2 A. J. Fatiadi and W. F. Sager (1973), Hexahydroxybenzene [Benzenehexol] Organic Syntheses, Coll. Vol. 5, p. 595
  2. ↑ Gerd Leston(1996), (Polyhydroxy)benzenes. In Kirk‑Othmer Encyclopedia of Chemical Technology, John Wiley & Sons. doi:10.1002/0471238961.1615122512051920.a01
  3. 1 2 J.I.G. Codagan, John Buckingham, Finlay J. MacDonald, P. H. Rhodes (1996), Dictionary of organic compounds. CRC Press. 9000 pages. ISBN 0-412-54090-8, ISBN 978-0-412-54090-5.
  4. ↑ HEXAPHENOL Basic information. Chemical Book. Accessed on 2009-07-05.
  5. ↑ Alexander J. Fatiadi; Horace S. Isbell; William F. Sager (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.
  6. 1 2 Sandeep Kumar (2006), Self-organization of disc-like molecules: chemical aspects. Chem. Soc. Rev., volume 35, 83–109. doi:10.1039/b506619k
  7. ↑ John A. Cowan, Judith A. K. Howard, Michael A. Leech, Horst Puschmann and Ian D. Williams (2001), Hexahydroxybenzene—2,2'-bipyridine (1/2). Acta Crystallographica Section C, volume C57, 1194–1195. doi:10.1107/S0108270101011350
  8. 1 2 Fèlix Serratosa (1983), Acetylene Diethers: A Logical Entry to Oxocarbons. Acc. Chem. Res. volume 16, pages 170--176. doi:10.1021/ar00089a004
  9. ↑ R. Nietzki and T. Benckiser (1885), Berichte Chemie, volume 18, page 1834. Cited by Fatiadi and Sanger.
  10. ↑ 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.
  11. ↑ Werner Büchner, E. Weiss (1964) Zur Kenntnis der sogenannten «Alkalicarbonyle» IV[1] Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid. Helvetica Chimica Acta, Volume 47 Issue 6, Pages 1415–1423. doi:10.1002/hlca.19640470604
  12. ↑ Haiyan Chen, Michel Armand, Matthieu Courty, Meng Jiang, Clare P. Grey, Franck Dolhem, Jean-Marie Tarascon, and Philippe Poizot (2009), Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery J. Am. Chem. Soc., 131 (25), pp. 8984–8988 doi:10.1021/ja9024897
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