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Revision as of 16:24, 27 November 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit		Latest revision as of 20:55, 29 November 2024 edit undo5.178.188.143 (talk) →BenzenehexolateTag: Visual edit
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	{{chembox		{{Chembox
			| Watchedfields = changed
	| verifiedrevid = 415896122		| verifiedrevid = 462751844
	| ImageFile = Benzenehexol.svg		| ImageFile = Benzenehexol.svg
	| ImageSize = 140px
	| ImageFile1 = Hexahydroxybenzene-3D-balls.png		| ImageSize = 140px
			| ImageFile1 = Hexahydroxybenzene-3D-balls.png
	| ImageSize1 = 160px		| ImageSize1 = 160px
			| PIN = Benzenehexol<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 693 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
	| IUPACName = benzene-1,2,3,4,5,6-hexol
			| 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
	| OtherNames = hexahydroxybenzene
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo=608-80-0		| CASNo = 608-80-0
	| PubChem=69102
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES=C1(=C(C(=C(C(=C1O)O)O)O)O)O
	| PubChem = 69102		| UNII = 80XJ9A89E2
	| ChemSpiderID = 62319		| PubChem = 69102
		⚫	| SMILES = c1(c(c(c(c(c1O)O)O)O)O)O
⚫	| InChI = 1/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| InChIKey = VWPUAXALDFFXJW-UHFFFAOYAU
			| ChemSpiderID = 62319
⚫	| StdInChI = 1S/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H
		⚫	| InChI = 1/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H
⚫	| StdInChIKey = VWPUAXALDFFXJW-UHFFFAOYSA-N
		⚫	| 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		|Section2={{Chembox Properties
			| C=6 | H=6 | O=6
	| Formula=C<sub>6</sub>H<sub>6</sub>O<sub>6</sub>
			| Appearance =
	| MolarMass=174.11
			| Density =
	| Appearance=
			| MeltingPt =
	| Density=
			| BoilingPt =
	| MeltingPt=
		⚫	| Solubility =
	| BoilingPt=
		⚫	}}
⚫	| Solubility=
⚫	}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards =
	| FlashPt=		| FlashPt =
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
			'''Benzenehexol''', also called '''hexahydroxybenzene''', is an ] with formula {{chem|C|6|H|6|O|6}} or {{chem|C|6|(OH)|6}}. It is a six-fold ] of ].<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}}</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''', also called '''hexahydroxybenzene''', is an ] with formula C<sub>6</sub>H<sub>6</sub>O<sub>6</sub> or C<sub>6</sub>(OH)<sub>6</sub>. It is a six-fold ] of ].<ref name="fati1">
	A. J. Fatiadi and W. F. Sager (1973), ''Hexahydroxybenzene '' Organic Syntheses, Coll. Vol. 5, p. 595
	</ref><ref name="lest">
	Gerd Leston(1996), ''(Polyhydroxy)benzenes''. In ''Kirk‑Othmer Encyclopedia of Chemical Technology'', John Wiley & Sons. {{doi|10.1002/0471238961.1615122512051920.a01}}
	</ref> The product is also erroneously called '''hexaphenol''',<ref name="coda">
	J.I.G. Codagan, John Buckingham, Finlay J. MacDonald, P. H. Rhodes (1996), ''Dictionary of organic compounds''. CRC Press. 9000 pages. ISBN 0412540908, 9780412540905
	</ref> but this name has been used also for other substances.<ref>
	. Chemical Book. Accessed on 2009-07-05.
	</ref>
	Benzenehexol is a crystalline solid soluble in hot water,<ref name="coda"/> with melting point higher than 310°.<ref name="fati1"/> It can be prepared from ] (cyclohexanehexol). Oxidation of benzenehexol yields ] (THBQ), ], and ].<ref name="fati2">		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 ] (cyclohexanehexol).{{cn|date=July 2024}} Oxidation of benzenehexol yields ] (THBQ), ], and ].<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 ] THBQ salt with ]/].<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 }}</ref>
	{{cite journal
	| title = Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)
	| author = Alexander J. Fatiadi
	| coauthors = Horace S. Isbell, William F. Sager
	| journal = Journal of Research of the National Bureau of Standards A: Physics and Chemistry
	| volume = 67A
	| issue = 2
	| month = March–April
	| url = http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf
	| year = 1963
	| pages = 153–162
	}}</ref> Conversely, benzenehexol can be obtained by reduction of ] THBQ salt with ]/].<ref name="kumar">
	Sandeep Kumar (2006), ''Self-organization of disc-like molecules: chemical aspects''. Chem. Soc. Rev., volume 35, 83–109. {{doi|10.1039/b506619k}}
	</ref>
	Benzenehexol is a starting material for a class of ].<ref name="kumar"/>		Benzenehexol is a starting material for a class of ].<ref name="Kumar2006" />
	Benzenehexol forms an ] with ], with 1:2 molecular ratio.<ref>		Benzenehexol forms an ] with ], 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>
	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.
	</ref>
	==Benzenehexolate==		==Benzenehexolate==
	Like most phenols, benzenehexol can lose the six ] ions from the ] groups yielding the ] C<sub>6</sub>O<sub>6</sub><sup>6&minus;</sup>. The ] salt of this anion is one of the components of ]'s so-called "potassium carbonyl", the product of the reaction of ] with potassium. The hexaanion is produced by trimerization of the ] anion {{chem|C|2|O|2|2-}} when heating potassium acetylenediolate {{chem|K|2|C|2|O|2}}.<ref name=serra>		Like most phenols, benzenehexol can lose the six ] ions from the ] groups, yielding the ] {{chem|C|6|O|6|6-}}. The ] salt of this anion is one of the components of ]'s so-called "potassium carbonyl", the product of the reaction of ] with potassium. The hexaanion is produced by trimerization of the ] 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 ] and {{Ill|Theodor Benckiser|de}} in 1885, who found that its ] 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}} at books.google.com, accessed on 2010-01-15.
	Fèlix Serratosa (1983), ''Acetylene Diethers: A Logical Entry to Oxocarbons''. Acc. Chem. Res volume 16, pages 170--176. {{doi|10.1021/ar00089a004}}
		⚫	</ref><ref name="wbuechIV"> {{cite journal | author = Büchner Werner, Weiss E | year = 1964 | title = Zur Kenntnis der sogenannten "Alkalicarbonyle" IV 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>
	</ref> The nature of {{chem|K|6|C|6|O|6}} was clarified by ] and ] in 1885, who found that its ] yielded benzenehexol.<ref name=nietzki>
	B. Nietzki and T. Benckiser (1885), Berichte Chemie, volume 18, page 1834. Cited by Fatiadi and Sanger.
	</ref><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 0415179122 at books.google.com, accessed on 2010-01-15.
	</ref><ref name="wbuechIV">
⚫	Werner Büchner, E. Weiss (1964) ''Zur Kenntnis der sogenannten «Alkalicarbonyle» IV Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid. Helvetica Chimica Acta, Volume 47 Issue 6, Pages 1415–1423. {{doi|10.1002/hlca.19640470604}}
	</ref>
	The ] salt of this anion, Li<sub>6</sub>C<sub>6</sub>O<sub>6</sub> has been considered for ] applications.<ref name="chen">		The ] salt of this anion, Li<sub>6</sub>C<sub>6</sub>O<sub>6</sub> has been considered for ] 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>
	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}}
	</ref>
	== Esters==		==Esters==
	hexahydroxy benzene forms esters such as the hexaacetate {{chem|C|6|O|6}}(-O(CO)CH<sub>3</sub>)<sub>6</sub> (melting point 220°C) and ethers like ] {{chem|C|6|O|6}}(-OC(CH<sub>3</sub>)<sub>3</sub>)<sub>6</sub> (melting point 223°C).<ref name=serra/>		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 ] {{chem|C|6}}(-OC(CH<sub>3</sub>)<sub>3</sub>)<sub>6</sub> (melting point 223&nbsp;°C).<ref name=serra/>
	==References==		==References==
	{{reflist}}		{{reflist}}
	]		]
	]
	]