Benzoquinonetetracarboxylic dianhydride

Summary

Benzoquinonetetracarboxylic dianhydride
Benzoquinonetetracarboxylic dianhydride.svg
Benzoquinonetetracarboxylic-dianhydride-3D-balls.png
Benzoquinonetetracarboxylic dianhydride molecule
Names
Preferred IUPAC name
1H,3H-Benzo[1,2-c:4,5-c′]difuran-1,3,4,5,7,8-hexone
Identifiers
  • 32192-32-8 ☒N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 32686035 ☒N
  • 85781674
  • InChI=1S/C10O8/c11-5-1-2(8(14)17-7(1)13)6(12)4-3(5)9(15)18-10(4)16 ☒N
    Key: NWWNDTOPIPOVFQ-UHFFFAOYSA-N ☒N
  • InChI=1/C10O8/c11-5-1-2(8(14)17-7(1)13)6(12)4-3(5)9(15)18-10(4)16
    Key: NWWNDTOPIPOVFQ-UHFFFAOYAX
  • O=C(C(C(O3)=O)=C1C3=O)C2=C(C(OC2=O)=O)C1=O
Properties
C10O8
Molar mass 248.102 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Benzoquinonetetracarboxylic dianhydride is an organic compound with formula C
10
O
8
(an oxide of carbon) which can be seen as the result of removing two molecules of water H
2
O
from benzoquinonetetracarboxylic acid.

It is a red solid, stable in dry air up to 140 °C and insoluble in ether, carbon tetrachloride, dichloromethane, and carbon disulfide. It reacts with acetone, ethyl acetate, tetrahydrofuran, ethanol, and water. It dissolves in methylated derivatives of benzene to give solutions ranging from orange to violet. When the molecule is exposed to moist air it quickly turns blue.

The compound was synthesized in 1963 by P. R. Hammond who claimed it was "one of the strongest π-electron acceptors so far described."[1]

See also

References

  1. ^ Hammond, P. R. (1963). "1,4-Benzoquinone Tetracarboxylic Acid Dianhydride, C1008:A Strong Acceptor". Science. 142 (3591): 502. doi:10.1126/science.142.3591.502. PMID 17748167.