Benzenehexol

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Benzenehexol
Benzenehexol.svg
Hexahydroxybenzene-3D-balls.png
Names
Preferred IUPAC name
Benzenehexol [1]
Other names
Benzene-1,2,3,4,5,6-hexol
Hexahydroxybenzene
2,3,4,5,6-pentahydroxyphenol
1,2,3,4,5,6-hexahydroxybenzene
Hexaphenol
Fenolão
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.204.877 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H Yes check.svgY
    Key: VWPUAXALDFFXJW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-12H
    Key: VWPUAXALDFFXJW-UHFFFAOYAU
  • c1(c(c(c(c(c1O)O)O)O)O)O
Properties
C6H6O6
Molar mass 174.108 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C
6
H
6
O
6
or C
6
(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]

Contents

Benzenehexol is a crystalline solid soluble in hot water, [4] with a melting point above 310°. [2] It can be prepared from inositol (cyclohexanehexol).[ citation needed ] 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

Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanion C
6
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 C
2
O2−
2
when heating potassium acetylenediolate K
2
C
2
O
2
. [9] The nature of K
6
C
6
O
6
was clarified [10] by Rudolf Nietzki and Theodor Benckiser  [ de ] in 1885, who found that its hydrolysis yielded benzenehexol. [11] [12]

The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications. [13]

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). [9]

Related Research Articles

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

In organic chemistry, a carbanion is an anion in which carbon is negatively charged.

In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. Haloarenes are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

Cuprates are a class of compounds that contain copper (Cu) atom(s) in an anion. They can be broadly categorized into two main types:

<span class="mw-page-title-main">Benzyl group</span> Chemical group (–CH₂–C₆H₅)

In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH2−C6H5. Benzyl features a benzene ring attached to a methylene group.

<span class="mw-page-title-main">Lithium diisopropylamide</span> Chemical compound

Lithium diisopropylamide is a chemical compound with the molecular formula LiN(CH 2)2. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.

<span class="mw-page-title-main">Ozonide</span> Polyatomic ion (O3, charge –1), or cyclic compounds made from ozone and alkenes

Ozonide is the polyatomic anion O−3. Cyclic organic compounds formed by the addition of ozone to an alkene are also called ozonides.

<span class="mw-page-title-main">Diazonium compound</span> Group of organonitrogen compounds

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N+≡N]X where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent compound where R is hydrogen, is diazenylium.

<span class="mw-page-title-main">Durene</span> Chemical compound

Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.

<span class="mw-page-title-main">L-selectride</span> Chemical compound

L-selectride is a organoboron compound with the chemical formula Li[(CH3CH2CH )3BH]. A colorless salt, it is usually dispensed as a solution in THF. As a particularly basic and bulky borohydride, it is used for stereoselective reduction of ketones.

<span class="mw-page-title-main">Dodecahydroxycyclohexane</span> Chemical compound

Dodecahydroxycyclohexane is an organic compound with molecular formula C6O12H12 or C6(OH)12 or (C 2)6. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone.

<span class="mw-page-title-main">Decahydroxycyclopentane</span> Chemical compound

Decahydroxycyclopentane is an organic compound with formula C5O10H10 or C5(OH)10. It is a fivefold geminal diol on a cyclopentane backbone.

<span class="mw-page-title-main">Tetrahydroxy-1,4-benzoquinone</span> Chemical compound

Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone, is an organic compound with formula C6O2(OH)4. Its molecular structure consists of a cyclohexadiene ring with four hydroxyl groups and two ketone groups in opposite (para) positions.

<span class="mw-page-title-main">Acetylenedicarboxylic acid</span> Chemical compound

Acetylenedicarboxylic acid or butynedioic acid is an organic compound with the formula H2C4O4 or HO−C(=O)−C≡C−C(=O)−OH. It is a crystalline solid that is soluble in diethyl ether.

<span class="mw-page-title-main">Croconate blue</span>

Croconate blue or 1,2,3-tris(dicyanomethylene)croconate is a divalent anion with chemical formula C
14
N
6
O2−
2
or ((N≡C−)2C=)3(C5O2)2−. It is one of the pseudo-oxocarbon anions, as it can be described as a derivative of the croconate oxocarbon anion C
5
O2−
5
through the replacement of three oxygen atoms by dicyanomethylene groups =C(−C≡N)2. The term Croconate Blue as a dye name specifically refers to the dipotassium salt K
2
C
14
N
6
O
2
.

<span class="mw-page-title-main">Hexamethylbenzene</span> Chemical compound

Hexamethylbenzene, also known as mellitene, is a hydrocarbon with the molecular formula C12H18 and the condensed structural formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each been replaced by a methyl group. In 1929, Kathleen Lonsdale reported the crystal structure of hexamethylbenzene, demonstrating that the central ring is hexagonal and flat and thereby ending an ongoing debate about the physical parameters of the benzene system. This was a historically significant result, both for the field of X-ray crystallography and for understanding aromaticity.

<span class="mw-page-title-main">Dimethylcadmium</span> Chemical compound

Dimethylcadmium is the organocadmium compound with the formula Cd(CH3)2. It is a colorless, highly toxic liquid that fumes in air. It is a linear molecule with C-Cd bond lengths of 213 pm. The compound finds limited use as a reagent in organic synthesis and in metalorganic chemical vapor deposition (MOCVD). It has also been used in the synthesis of cadmium selenide nanoparticles, although efforts have been made to replace it in this capacity due to its toxicity.

Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, Leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib and triflurazin. A relevant agrochemical is trifluralin. The development of synthetic methods for adding trifluoromethyl groups to chemical compounds is actively pursued in academic research.

<span class="mw-page-title-main">Tetramethyldiborane</span> Chemical compound

Dimethylborane, (CH3)2BH is the simplest dialkylborane, consisting of a methyl group substituted for a hydrogen in borane. As for other boranes it normally exists in the form of a dimer called tetramethyldiborane or tetramethylbisborane or TMDB ((CH3)2BH)2. Other combinations of methylation occur on diborane, including monomethyldiborane, trimethyldiborane, 1,2-dimethylborane, 1,1-dimethylborane and trimethylborane. At room temperature the substance is at equilibrium between these forms. The methylboranes were first prepared by H. I. Schlesinger and A. O. Walker in the 1930s.

Germyl, trihydridogermanate(1-), trihydrogermanide, trihydridogermyl or according to IUPAC Red Book: germanide is an anion containing germanium bounded with three hydrogens, with formula GeH−3. Germyl is the IUPAC term for the –GeH3 group. For less electropositive elements the bond can be considered covalent rather than ionic as "germanide" indicates. Germanide is the base for germane when it loses a proton.

References

  1. "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.
  2. 1 2 Fatiadi, Alexander J.; Sager, William F. "Hexahydroxybenzene (Benzenehexol)". Organic Syntheses. Retrieved 2023-01-28.
  3. Leston, Gerd (2000-12-04), "(Polyhydroxy)benzenes", in John Wiley & Sons, Inc. (ed.), Kirk-Othmer Encyclopedia of Chemical Technology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 1615122512051920.a01, doi:10.1002/0471238961.1615122512051920.a01, ISBN   978-0-471-23896-6 , retrieved 2023-01-28
  4. 1 2 Codagan, J.I.G.; Buckingham, John; MacDonald, Finlay J.; Rhodes, P. H. (1996). Dictionary of Organic Compounds, 6th edition. London: Chapman & Hall; CRC Press. ISBN   9780412540905. OCLC   35716592.
  5. "Hexaphenol (CAS: 1506-76-9)". www.chemicalbook.com. Retrieved 2009-07-05.
  6. Fatiadi, Alexander J.; Isbell, Horace S.; Sager, William F. (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.
  7. 1 2 Kumar, Sandeep (2006). "Self-organization of disc-like molecules: chemical aspects". Chemical Society Reviews. 35 (1): 83–109. doi:10.1039/b506619k. PMID   16365644.
  8. 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. PMID   11600782. S2CID   25797464.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. 1 2 Serratosa Fèlix (1983). "Acetylene Diethers: A Logical Entry to Oxocarbons". Acc. Chem. Res. 16 (5): 170–176. doi:10.1021/ar00089a004.
  10. R. Nietzki; Th. Benckiser (1885). "Ueber Hexaoxybenzolderivate und ihre Beziehungen zur Krokonsäure und Rhodizonsäure". Berichte der Deutschen Chemischen Gesellschaft (in German). 18 (1): 499–515. doi:10.1002/CBER.188501801110. ISSN   0365-9496. Wikidata   Q56853054.
  11. 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.
  12. 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.
  13. 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)