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Duroquinone

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Duroquinone
Structural formula of duroquinone
Ball-and-stick model of the duroquinone molecule
Names
Preferred IUPAC name 2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-dione
Other names 2,3,5,6-Tetramethyl-1,4-benzoquinone
Tetramethyl-p-benzoquinone
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1909128
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.646 Edit this at Wikidata
EC Number
  • 208-409-8
Gmelin Reference 279610
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3Key: WAMKWBHYPYBEJY-UHFFFAOYSA-N
  • InChI=1/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3Key: WAMKWBHYPYBEJY-UHFFFAOYAK
SMILES
  • CC1=C(C(=O)C(=C(C1=O)C)C)C
Properties
Chemical formula C10H12O2
Molar mass 164.20408 g/mol
Melting point 109 to 114 °C (228 to 237 °F; 382 to 387 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Duroquinone is an organic oxidant (C6(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.

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

A derived organoiron compound (η,η-C6(CH3)4O2)Fe(CO)3 is obtained by the carbonylation of 2-butyne in the presence of iron pentacarbonyl.

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

Duroquinone was observed in a degradation products generated from pyrolysis of α-Tocopheryl acetate.

References

  1. J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.doi:10.1021/ja066471o
  2. Lee Irvin Smith. (1943). "Duronquinone". Organic Syntheses; Collected Volumes, vol. 2, p. 254.
  3. H. W. Sternberg, R. Markby and I. Wender, "A Quinone Iron Tricarbonyl Complex and its Significance in Organic Synthesis", Journal of the American Chemical Society 1958 volume 80, pp. 1009-1010. doi:10.1021/ja01537a075
  4. *Fildes, Jonathan (2008-03-11). "Chemical brain controls nanobots". British Broadcasting Corporation. Retrieved 2008-03-11.
  5. Wu, Dan; O’Shea, Donal F. (2020-03-24). "Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate". Proceedings of the National Academy of Sciences. 117 (12): 6349–6355. doi:10.1073/pnas.1920925117. ISSN 0027-8424. PMC 7104367. PMID 32156732.


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