{{Chembox | Watchedfields = changed | verifiedrevid = 462751844 | ImageFile = Benzenehexol.svg | ImageSize = 140px | ImageName = Skeletal formula | ImageClass = skin-invert | ImageFile1 = Hexahydroxybenzene-3D-balls.png | ImageSize1 = 160px | ImageClass1 = bg-transparent | PIN = Benzenehexol<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 693 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> | OtherNames = Benzene-1,2,3,4,5,6-hexol<br />Hexahydroxybenzene<br />2,3,4,5,6-pentahydroxyphenol<br />1,2,3,4,5,6-hexahydroxybenzene<br />Hexaphenol<br />Fenolão |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 608-80-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 80XJ9A89E2 | PubChem = 69102 | SMILES = c1(c(c(c(c(c1O)O)O)O)O)O | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 62319 | InChI = 1/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H | InChIKey = VWPUAXALDFFXJW-UHFFFAOYAU | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VWPUAXALDFFXJW-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=6 | H=6 | O=6 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Benzenehexol''', also called '''hexahydroxybenzene''', is an organic compound with formula {{chem2|C6H6O6|auto=1}} or {{chem|C|6|(OH)|6}}. It is a six-fold phenol of benzene.<ref name="Fatiadi1962">{{Cite web |first1=Alexander J. |last1=Fatiadi |first2=William F. |last2=Sager |title=Hexahydroxybenzene (Benzenehexol) |url=https://orgsyn.org/demo.aspx?prep=cv5p0595 |access-date=2023-01-28 |website=Organic Syntheses}}</ref><ref name="lest">{{Citation |last=Leston |first=Gerd |title=(Polyhydroxy)benzenes |date=2000-12-04 |url=https://onlinelibrary.wiley.com/doi/10.1002/0471238961.1615122512051920.a01 |encyclopedia=Kirk-Othmer Encyclopedia of Chemical Technology |pages=1615122512051920.a01 |editor-last=John Wiley & Sons, Inc. |place=Hoboken, NJ, USA |publisher=John Wiley & Sons, Inc. |language=en |doi=10.1002/0471238961.1615122512051920.a01 |isbn=978-0-471-23896-6 |access-date=2023-01-28|url-access=subscription }}</ref> The product is also called '''hexaphenol''',<ref name="Codagan1996">{{cite book|first1=J.I.G. |last1=Codagan |first2=John |last2=Buckingham |first3=Finlay J. |last3=MacDonald |first4=P. H. |last4=Rhodes |year=1996 |title=Dictionary of Organic Compounds, 6th edition |publisher=Chapman & Hall; CRC Press |location=London |oclc=35716592 |isbn=9780412540905}}</ref> but this name has been used also for other substances.<ref>{{cite web |title=Hexaphenol (CAS: 1506-76-9) |url=https://www.chemicalbook.com/ProductChemicalPropertiesCB7111482_EN.htm |access-date= 2009-07-05 |website=www.chemicalbook.com}}</ref>

Benzenehexol is a crystalline solid soluble in hot water,<ref name="Codagan1996" /> with a melting point above 310°.<ref name="Fatiadi1962" /> It can be prepared from inositol (cyclohexanehexol).{{cn|date=July 2024}} Oxidation of benzenehexol yields tetrahydroxy-''p''-benzoquinone (THBQ), rhodizonic acid, and dodecahydroxycyclohexane.<ref name="Fatiadi1963">{{cite journal |title= Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol) |first1=Alexander J. |last1=Fatiadi |first2= Horace S. |last2=Isbell |first3=William F. |last3=Sager |journal= Journal of Research of the National Bureau of Standards Section A |volume= 67A |issue=2 |date=March–April 1963 |url= http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf |pages= 153–162 |doi= 10.6028/jres.067A.015 |access-date= 2009-07-05 |archive-url= https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf |archive-date= 2009-03-25 |url-status=dead |pmid= 31580622 |pmc= 6640573}}</ref> Conversely, benzenehexol can be obtained by reduction of sodium THBQ salt with SnCl<sub>2</sub>/HCl.<ref name="Kumar2006">{{cite journal | last = Kumar | first = Sandeep | year = 2006 | title = Self-organization of disc-like molecules: chemical aspects | url = https://pubs.rsc.org/en/content/articlelanding/2006/cs/b506619k | journal = Chemical Society Reviews | volume = 35 | issue = 1| pages = 83–109 | doi = 10.1039/b506619k| pmid = 16365644 | url-access = subscription }}</ref>

Benzenehexol is a starting material for a class of discotic liquid crystals.<ref name="Kumar2006" />

Benzenehexol forms an adduct with 2,2'-bipyridine, with 1:2 molecular ratio.<ref> {{cite journal | author = Cowan John A., Howard Judith A. K., Leech Michael A., Puschmann Horst, Williams Ian D. | year = 2001 | title = ''Hexahydroxybenzene—2,2'-bipyridine (1/2)'' | journal = Acta Crystallographica Section C | volume = 57| issue = 10| pages = 1194–1195| doi = 10.1107/S0108270101011350 | pmid = 11600782 | s2cid = 25797464 }}</ref>

==Benzenehexolate== Like most phenols, benzenehexol can lose the six H<sup>+</sup> ions from the hydroxyl groups, yielding the hexaanion {{chem|C|6|O|6|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 {{chem|C|2|O|2|2-}} when heating potassium acetylenediolate {{chem|K|2|C|2|O|2}}.<ref name=serra> {{cite journal | author = Serratosa Fèlix | year = 1983 | title = Acetylene Diethers: A Logical Entry to Oxocarbons | journal = Acc. Chem. Res. | volume = 16| issue = 5| pages = 170–176| doi = 10.1021/ar00089a004 }}</ref> The nature of {{chem|K|6|C|6|O|6}} was clarified<ref>{{Cite Q|Q56853054}}</ref> by Rudolf Nietzki and {{Ill|Theodor Benckiser|de}} in 1885, who found that its hydrolysis yielded benzenehexol.<ref name=mond> 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}} [https://books.google.com/books?id=F7XSYSB1-NYC&pg=PA326 Online version] at books.google.com, accessed on 2010-01-15. </ref><ref name="wbuechIV"> {{cite journal | author = Büchner Werner, Weiss E | year = 1964 | title = Zur Kenntnis der sogenannten "Alkalicarbonyle" IV[1] Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid | journal = Helvetica Chimica Acta | volume = 47| issue = 6| pages = 1415–1423| doi = 10.1002/hlca.19640470604 }}</ref>

The lithium salt of this anion, Li<sub>6</sub>C<sub>6</sub>O<sub>6</sub> has been considered for electric battery applications.<ref name="chen"> {{cite journal | author = Chen Haiyan, Armand Michel, Courty Matthieu, Jiang Meng, Grey Clare P., Dolhem Franck, Tarascon Jean-Marie, Poizot Philippe | year = 2009 | title = Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery | journal = J. Am. Chem. Soc. | volume = 131| issue = 25| pages = 8984–8988| doi = 10.1021/ja9024897 | pmid = 19476355 }}</ref>

==Esters== Hexahydroxy benzene forms esters such as the hexaacetate {{chem|C|6}}(-O(CO)CH<sub>3</sub>)<sub>6</sub> (melting point 220&nbsp;°C) and ethers like hexa-tert-butoxybenzene {{chem|C|6}}(-OC(CH<sub>3</sub>)<sub>3</sub>)<sub>6</sub> (melting point 223&nbsp;°C).<ref name=serra/>

==References== {{reflist}}

Category:Polyphenols