Duroquinone

Title: Duroquinone
CAS Registry Number: 527-17-3
CAS Name: 2,3,5,6-Tetramethyl-2,5-cyclohexadiene-1,4-dione
Additional Names: tetramethyl-p-benzoquinone
Molecular Formula: C10H12O2
Molecular Weight: 164.20
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature References: Prepn by reduction of dinitrodurene: Smith, Org. Synth. vol. 10, 40 (1930); Smith, Dobrovolny, J. Am. Chem. Soc. 48, 1420 (1926); by condensation of 2,3-diketopentane with itself in presence of alkalies: von Pechmann, Ber. 21, 1420 (1888); by the action of alkalies on 3,3-dichloropentan-2-one: Faworsky, J. Prakt. Chem. [2] 51, 538 (1895).
Properties: Yellow needles from alc, mp 111-112°. Sublimes. Volatile with steam. Insol in water; sol in alcohol, benzene, ether, hot petr ether.
Melting point: mp 111-112°
Dutasteride Duthaler-Hafner Reagent d-Verbenone Dyclonine Dydrogesterone

Duroquinone
Duroquinone.png
Identifiers
CAS number 527-17-3 YesY
ChemSpider 61539 YesY
UNII X0Q8791R69 YesY
DrugBank DB01927
ChEBI CHEBI:42023 YesY
ChEMBL CHEMBL151604 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H12O2
Molar mass 164.20408 g/mol
Melting point 109 - 114 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Duroquinone is the organic compound with the formula C4(CH3)4O2. It is related to 1,4-benzoquinone by replacement of four H centres with methyl (Me) groups. The C10O2 core of this molecule is planar with two pairs of C=O and C=C bonds.[1]

The compound is produced via nitration of durene (1,2,4,5-tetramethylbenzene) followed reduction to the diamine and then oxidation.[2]

A derived organoiron compound (η22-C4(CH3)4O2)Fe(CO)3 is obtained by the carbonylation of 2-butyne in the presence of iron pentacarbonyl.[3]

The molecule has been mentioned in the popular press as a component of a "nano brain".[4]