Benzenehexol Explained

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula or . It is a six-fold phenol of benzene.^[1] The product is also called hexaphenol,^[2] but this name has been used also for other substances.^[3]

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.^[4] Conversely, benzenehexol can be obtained by reduction of sodium THBQ salt with SnCl₂/HCl.^[5]

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.^[6]

Benzenehexolate

Like most phenols, benzenehexol can lose the six H⁺ ions from the hydroxyl groups, yielding the hexaanion . 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 when heating potassium acetylenediolate .^[7] The nature of was clarified by R. Nietzki and T. Benckiser in 1885, who found that its hydrolysis yielded benzenehexol.^{[8] [9] [10]}

The lithium salt of this anion, Li₆C₆O₆ has been considered for electric battery applications.^[11]

Esters

Hexahydroxy benzene forms esters such as the hexaacetate (-O(CO)CH₃)₆ (melting point 220 °C) and ethers like hexa-tert-butoxybenzene (-OC(CH₃)₃)₆ (melting point 223 °C).^[7]

Notes and References

1. Web site: Alexander J. . Fatiadi . William F. . Sager . Hexahydroxybenzene (Benzenehexol) . 2023-01-28 . Organic Syntheses.
2. Book: J.I.G. . Codagan . John . Buckingham . Finlay J. . MacDonald . P. H. . Rhodes . 1996 . Dictionary of Organic Compounds, 6th edition . Chapman & Hall; CRC Press . London . 35716592 . 9780412540905.
3. Web site: Hexaphenol (CAS: 1506-76-9) . 2009-07-05 . www.chemicalbook.com.
4. Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol) . Alexander J. . Fatiadi . Horace S. . Isbell . William F. . Sager . Journal of Research of the National Bureau of Standards Section A . 67A . 2 . March–April 1963 . 153–162 . 10.6028/jres.067A.015 . 2009-07-05 . https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf . 2009-03-25 . dead . 31580622 . 6640573.
5. Kumar . Sandeep . 2006 . Self-organization of disc-like molecules: chemical aspects . Chemical Society Reviews . 35 . 1. 83–109 . 10.1039/b506619k. 16365644 .
6. 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. 10.1107/S0108270101011350 . 11600782 . 25797464 .
7. Serratosa Fèlix . 1983 . Acetylene Diethers: A Logical Entry to Oxocarbons . Acc. Chem. Res. . 16. 5. 170–176. 10.1021/ar00089a004 .
8. R. Nietzki and T. Benckiser (1885), Berichte Chemie, volume 18, page 1834. Cited by Fatiadi and Sanger.
9. 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). Online version at books.google.com, accessed on 2010-01-15.
10. 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. 10.1002/hlca.19640470604 .
11. 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. 10.1021/ja9024897 . 19476355 .