Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C6H6O6 or C6(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]
Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanionC 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]
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
^"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. ISBN978-0-85404-182-4.
^ ab A. J. Fatiadi and W. F. Sager (1973), Hexahydroxybenzene [Benzenehexol] Organic Syntheses, Coll. Vol. 5, p. 595
^ Gerd Leston(1996), (Polyhydroxy)benzenes. In Kirk‑Othmer Encyclopedia of Chemical Technology, John Wiley & Sons. doi:10.1002/0471238961.1615122512051920.a01
^ ab J.I.G. Codagan, John Buckingham, Finlay J. MacDonald, P. H. Rhodes (1996), Dictionary of organic compounds. CRC Press. 9000 pages. ISBN0-412-54090-8, ISBN978-0-412-54090-5.
^ HEXAPHENOL Basic information. Chemical Book. Accessed on 2009-07-05.
^Alexander J. Fatiadi; Horace S. Isbell; William F. Sager (March–April 1963). (PDF). Journal of Research of the National Bureau of Standards Section A. 67A (2): 153–162. doi:10.6028/jres.067A.015. PMC6640573. PMID 31580622. Archived from the original (PDF) on 2009-03-25. Retrieved 2009-07-05.
^ ab Kumar Sandeep (2006). "Self-organization of disc-like molecules: chemical aspects". Chem. Soc. Rev. 35 (1): 83–109. doi:10.1039/b506619k.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ab Serratosa Fèlix (1983). "Acetylene Diethers: A Logical Entry to Oxocarbons". Acc. Chem. Res. 16 (5): 170–176. doi:10.1021/ar00089a004.
^ R. Nietzki and T. Benckiser (1885), Berichte Chemie, volume 18, page 1834. Cited by Fatiadi and Sanger.
^ 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). ISBN0-415-17912-2 Online version at books.google.com, accessed on 2010-01-15.
^ 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.
^ 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)
January 06, 2023
benzenehexol, also, called, hexahydroxybenzene, organic, compound, with, formula, c6h6o6, fold, phenol, benzene, product, also, called, hexaphenol, this, name, been, used, also, other, substances, namespreferred, iupac, name, other, names, benzene, hexolhexahy. Benzenehexol also called hexahydroxybenzene is an organic compound with formula C6H6O6 or C6 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 NamesPreferred IUPAC name Benzenehexol 1 Other names Benzene 1 2 3 4 5 6 hexolHexahydroxybenzene2 3 4 5 6 pentahydroxyphenol1 2 3 4 5 6 hexahydroxybenzeneHexaphenolIdentifiersCAS Number 608 80 0 Y3D model JSmol Interactive imageChemSpider 62319 YECHA InfoCard 100 204 877PubChem CID 69102UNII 80XJ9A89E2 YCompTox Dashboard EPA DTXSID0060563InChI InChI 1S C6H6O6 c7 1 2 8 4 10 6 12 5 11 3 1 9 h7 12H YKey VWPUAXALDFFXJW UHFFFAOYSA N YInChI 1 C6H6O6 c7 1 2 8 4 10 6 12 5 11 3 1 9 h7 12HKey VWPUAXALDFFXJW UHFFFAOYAUSMILES c1 c c c c c1O O O O O OPropertiesChemical formula C6H6O6Molar mass 174 11Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references 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 EditLike most phenols benzenehexol can lose the six H ions from the hydroxyl groups yielding the hexaanion C6 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 C2 O2 2 when heating potassium acetylenediolate K2 C2 O2 9 The nature of K6 C6 O6 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 EditHexahydroxy benzene forms esters such as the hexaacetate C6 O CO CH3 6 melting point 220 C and ethers like hexa tert butoxybenzene C6 OC CH3 3 6 melting point 223 C 9 References Edit 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 a b A J Fatiadi and W F Sager 1973 Hexahydroxybenzene Benzenehexol Organic Syntheses Coll Vol 5 p 595 Gerd Leston 1996 Polyhydroxy benzenes In Kirk Othmer Encyclopedia of Chemical Technology John Wiley amp Sons doi 10 1002 0471238961 1615122512051920 a01 a b 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 HEXAPHENOL Basic information Chemical Book Accessed on 2009 07 05 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 PMC 6640573 PMID 31580622 Archived from the original PDF on 2009 03 25 Retrieved 2009 07 05 a b Kumar Sandeep 2006 Self organization of disc like molecules chemical aspects Chem Soc Rev 35 1 83 109 doi 10 1039 b506619k 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link a b Serratosa Felix 1983 Acetylene Diethers A Logical Entry to Oxocarbons Acc Chem Res 16 5 170 176 doi 10 1021 ar00089a004 R Nietzki and T Benckiser 1885 Berichte Chemie volume 18 page 1834 Cited by Fatiadi and Sanger 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 Buchner Werner Weiss E 1964 Zur Kenntnis der sogenannten Alkalicarbonyle IV 1 Uber die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid Helvetica Chimica Acta 47 6 1415 1423 doi 10 1002 hlca 19640470604 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Retrieved from https en wikipedia org w index php title Benzenehexol amp 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