Benzoquinonetetracarboxylic dianhydride

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Benzoquinonetetracarboxylic dianhydride
Benzoquinonetetracarboxylic dianhydride.svg
Benzoquinonetetracarboxylic-dianhydride-3D-balls.png
Benzoquinonetetracarboxylic dianhydride molecule Benzoquinonetetracarboxylic-dianhydride-3D-spacefill.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
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C10O8/c11-5-1-2(8(14)17-7(1)13)6(12)4-3(5)9(15)18-10(4)16 X mark.svgN
    Key: NWWNDTOPIPOVFQ-UHFFFAOYSA-N X mark.svgN
  • 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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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

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1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula C6H4O2. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and ethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

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Dodecahydroxycyclohexane Chemical compound

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Benzenehexol Chemical compound

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C6H6O6 or C6(OH)6. It is a six-fold phenol of benzene. The product is also called hexaphenol, but this name has been used also for other substances.

Tetrahydroxy-1,4-benzoquinone 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.

A hydroxybenzoquinone is any of several organic compounds that can be viewed as derivatives of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).

Tetrahydroxy-1,4-benzoquinone bisoxalate Chemical compound

Tetrahydroxy-1,4-benzoquinone bisoxalate is a chemical compound, an oxide of carbon with formula C
10
O
10
. Its molecule consists of a 1,4-benzoquinone core with the four hydrogen atoms replaced by two oxalate groups. It can be seen as a fourfold ester of tetrahydroxy-1,4-benzoquinone and oxalic acid.

Benzoquinonetetracarboxylic acid Chemical compound

In chemistry, 1,4-benzoquinonetetracarboxylic acid is an organic compound with formula C
10
H
4
O
10
, or (C6O2)(-(CO)OH)4, which can be viewed as deriving from para-benzoquinoneC
6
H
4
O
2
through replacement of the four hydrogen atoms by carboxyl functional groups -(CO)OH.

Tetrahydroxy-1,4-benzoquinone biscarbonate Chemical compound

Tetrahydroxy-1,4-benzoquinone biscarbonate is a chemical compound, an oxide of carbon with formula C
8
O
8
. Its molecule consists of a 1,4-benzoquinone core with the four hydrogen atoms replaced by two carbonate groups. It can be seen as a fourfold ester of tetrahydroxy-1,4-benzoquinone and carbonic acid.

Hexahydroxybenzene trisoxalate Chemical compound

Hexahydroxybenzene trisoxalate is a chemical compound, an oxide of carbon with formula C
12
O
12
. Its molecule consists of a benzene core with the six hydrogen atoms replaced by three oxalate groups. It can be seen as a sixfold ester of benzenehexol and oxalic acid.

Hexahydroxybenzene triscarbonate Chemical compound

Hexahydroxybenzene triscarbonate is a chemical compound, an oxide of carbon with formula C
9
O
9
. Its molecular structure consists of a benzene core with the six hydrogen atoms replaced by three carbonate groups. It can be seen as a sixfold ester of hexahydroxybenzene (benzenehexol) and carbonic acid.

References

  1. Hammond, P. R. (1963). "1,4-Benzoquinone Tetracarboxylic Acid Dianhydride, C1008:A Strong Acceptor". Science. 142 (3591): 502. Bibcode:1963Sci...142..502H. doi:10.1126/science.142.3591.502. PMID   17748167. S2CID   9430830.