Tetrahydroxy-1,4-benzoquinone bisoxalate

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Tetrahydroxy-1,4-benzoquinone bisoxalate
Tetrahydroxybenzoquinone bisoxalate.svg
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Names
Preferred IUPAC name
Benzo[1,2-b:4,5-b′]bis([1,4]dioxine)hexone
Other names
Benzo[1,2-b:4,5-b']bis-p-dioxin-2,3,5,7,8,10-hexone (8CI)
Identifiers
3D model (JSmol)
PubChem CID
  • O=C1C(OC2=O)=C(OC2=O)C(C3=C1OC(C(O3)=O)=O)=O
Properties
C10O10
Molar mass 280.00 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

The compound was first described by H. S. Verter, H. Porter, and R. Dominic in 1968. It was obtained by reacting tetrahydroxy-1,4-benzoquinone with oxalyl chloride in tetrahydrofuran. It is a yellow solid that can be crystallized as a tetrahydrofuran solvate, but could not be prepared in pure form. [1]

See also

Related Research Articles

The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

<span class="mw-page-title-main">Hafnium tetrachloride</span> Chemical compound

Hafnium(IV) chloride is the inorganic compound with the formula HfCl4. This colourless solid is the precursor to most hafnium organometallic compounds. It has a variety of highly specialized applications, mainly in materials science and as a catalyst.

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

<span class="mw-page-title-main">Zirconium(IV) chloride</span> Chemical compound

Zirconium(IV) chloride, also known as zirconium tetrachloride, is an inorganic compound frequently used as a precursor to other compounds of zirconium. This white high-melting solid hydrolyzes rapidly in humid air.

<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

<span class="mw-page-title-main">Trimethylsilyl cyanide</span> Chemical compound

Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:

<span class="mw-page-title-main">Oxocarbon</span> Chemical compounds made of only carbon and oxygen

In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide. Many other stable or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide and mellitic anhydride.

<span class="mw-page-title-main">Dodecahydroxycyclohexane</span> Chemical compound

Dodecahydroxycyclohexane is an organic compound with molecular formula C6O12H12 or C6(OH)12 or (C 2)6. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone.

<span class="mw-page-title-main">Benzenehexol</span> Chemical compound

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C
6
H
6
O
6
or C
6
(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.

<span class="mw-page-title-main">Tetrahydroxy-1,4-benzoquinone</span> 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.

<span class="mw-page-title-main">Hydroxyquinone</span> Class of chemical compounds

Hydroxyquinone often refers to a hydroxybenzoquinone, any organic compound with formula C
6
H
4
O
3
which can be viewed as a derivative of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH). When unqualified, the terms usually mean specifically the compound 2-hydroxy-1,4-benzoquinone, derived from 1,4-benzoquinone or para-benzoquinone.

2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with formula C
6
H
4
O
4
, formally derived from 1,4-benzoquinone by replacing two hydrogen atoms with hydroxyl (OH) groups. It is one of seven dihydroxybenzoquinone isomers. It is a yellow solid with planar molecules that exhibits ferroelectric properties.

<span class="mw-page-title-main">Hydroxy-1,4-benzoquinone</span> Chemical compound

Hydroxy-1,4-benzoquinone, also called hydroxy-para-benzoquinone, is an organic compound with formula C
6
H
4
O
3
, formally derived from 1,4-Benzoquinone by replacing one hydrogen atom with a hydroxyl (OH) group. It is one of three hydroxybenzoquinone isomers and one of the simplest hydroxyquinones.

<span class="mw-page-title-main">Benzoquinonetetracarboxylic acid</span> 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.

<span class="mw-page-title-main">Benzoquinonetetracarboxylic dianhydride</span> Chemical compound

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

<span class="mw-page-title-main">Tetrahydroxy-1,4-benzoquinone biscarbonate</span> 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.

<span class="mw-page-title-main">Hexahydroxybenzene trisoxalate</span> 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.

<span class="mw-page-title-main">Hexahydroxybenzene triscarbonate</span> 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.

<span class="mw-page-title-main">1,4-Naphthoquinone</span> Chemical compound

1,4-Naphthoquinone or para-naphthoquinone is a quinone derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit. It is an isomer of 1,2-naphthoquinone.

Protactinium compounds are compounds containing the element protactinium. These compounds usually have protactinium in the +5 oxidation state, although these compounds can also exist in the +2, +3 and +4 oxidation states.

References

  1. H. S. Verter, H. Porter, and R. Dominic (Verter, Porter and Dominic, 1968), A new carbon oxide: synthesis of tetrahydroxybenzoquinone bisoxalate. Chemical Communications, p. 973b–974. doi : 10.1039/C1968000973b