Benzoquinonetetracarboxylic acid

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

Benzoquinone­tetracarboxylic acid

Names
Preferred IUPAC name 3,6-Dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylic acid
Identifiers
CAS Number	500797-27-3 N[GSRS]
3D model (JSmol)	Interactive image
ChemSpider	310781 N
PubChem CID	350050
UNII	5BE47MRU9L
CompTox Dashboard (EPA)	DTXSID101029309
InChI InChI=1S/C10H4O10/c11-5-1(7(13)14)2(8(15)16)6(12)4(10(19)20)3(5)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20) N Key: DMCTUEIMZPODLV-UHFFFAOYSA-N N InChI=1/C10H4O10/c11-5-1(7(13)14)2(8(15)16)6(12)4(10(19)20)3(5)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20) Key: DMCTUEIMZPODLV-UHFFFAOYAE
SMILES C1(=C(C(=O)C(=C(C1=O)C(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
Chemical formula	C10H4O10
Molar mass	284.14 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

By removal of four protons, the acid is expected to yield the anion C
₁₀O⁴⁻
₁₀, benzoquinonetetracarboxylate, which is one of the oxocarbon anions (consisting solely of oxygen and carbon). By loss of 1 through 3 protons, it forms the anions C
₁₀H
₃O⁻
₁₀, C
₁₀H
₂O²⁻
₁₀, and C
₁₀HO³⁻
₁₀, called respectively trihydrogen-, dihydrogen-, and hydrogenbenzoquinonetetracarboxylate. The same names are used for the corresponding esters.

Removal of two water molecules gives the compound benzoquinonetetracarboxylic dianhydride, C
₁₀O
₈, one of the oxides of carbon.^[1]

The acid can be obtained by from durene (1,2,4,5-tetramethylbenzene) via dinitropyromellitic and diaminopyromellitic acids.^[2][3][4]

See also

• Mellitic acid C
  ₁₂H
  ₆O
  ₁₂
• Tetrahydroxybenzoquinone C
  ₆H
  ₄O
  ₆
• Benzenehexol C
  ₆H
  ₆O
  ₆