Names | |
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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 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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). |
Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C
6H
6O
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]
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]
Like most phenols, benzenehexol can lose the six H+ ions from the hydroxyl groups, yielding the hexaanion C
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]
The lithium salt of this anion, Li6C6O6 has been considered for electric battery applications. [13]
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]
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.
In organic chemistry, a carbanion is an anion in which carbon is negatively charged.
In chemistry, a polyoxometalate is a polyatomic ion, usually an anion, that consists of three or more transition metal oxyanions linked together by shared oxygen atoms to form closed 3-dimensional frameworks. The metal atoms are usually group 6 or less commonly group 5 transition metals and Tc in their high oxidation states. Polyoxometalates are often colorless, orange or red diamagnetic anions. Two broad families are recognized, isopolymetalates, composed of only one kind of metal and oxide, and heteropolymetalates, composed of one metal, oxide, and a main group oxyanion. Many exceptions to these general statements exist.
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. The haloarene 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.
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 group.
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.
Biphenyl is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen may use the prefixes xenyl or diphenylyl.
Organoboron chemistry or organoborane chemistry is the chemistry of organoboron compounds or organoboranes, which are chemical compounds of boron and carbon that are organic derivatives of borane (BH3), for example trialkyl boranes..
Ozonide is the polyatomic anion O−3. Cyclic organic compounds formed by the addition of ozone to an alkene are also called ozonides.
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.
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.
Rhodizonic acid is a chemical compound with formula H2C6O6 or (CO)4(COH)2. It can be seen as a twofold enol and fourfold ketone of cyclohexene, more precisely 5,6-dihydroxycyclohex-5-ene-1,2,3,4-tetrone.
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.
Croconate blue or 1,2,3-tris(dicyanomethylene)croconate is a divalent anion with chemical formula C
14N
6O2−
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
5O2−
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
2C
14N
6O
2.
Organoplatinum chemistry is the chemistry of organometallic compounds containing a carbon to platinum chemical bond, and the study of platinum as a catalyst in organic reactions. Organoplatinum compounds exist in oxidation state 0 to IV, with oxidation state II most abundant. The general order in bond strength is Pt-C (sp) > Pt-O > Pt-N > Pt-C (sp3). Organoplatinum and organopalladium chemistry are similar, but organoplatinum compounds are more stable and therefore less useful as catalysts.
The Birch reduction is an organic reaction that is used to convert arenes to 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent with an alkali metal and a proton source. Unlike catalytic hydrogenation, Birch reduction does not reduce the aromatic ring all the way to a cyclohexane.
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.
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.
In organometallic chemistry, metal–halogen exchange is a fundamental reaction that converts an organic halide into an organometallic product. The reaction commonly involves the use of electropositive metals and organochlorides, bromides, and iodides. Particularly well-developed is the use of metal–halogen exchange for the preparation of organolithium compounds.
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