Furantetracarboxylic acid

Furantetracarboxylic acid
Names
	IUPAC name furan-2,3,4,5-tetracarboxylic acid
Identifiers
CAS Number	20416-04-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	207476;
PubChem CID	237617;
CompTox Dashboard (EPA)	DTXSID40285293 ;
	InChI InChI=1S/C8H4O9/c9-5(10)1-2(6(11)12)4(8(15)16)17-3(1)7(13)14/h(H,9,10)(H,11,12)(H,13,14)(H,15,16) Key: IREPGQRTQFRMQR-UHFFFAOYSA-N;
	SMILES C1(=C(OC(=C1C(=O)O)C(=O)O)C(=O)O)C(=O)O;
Properties
Chemical formula	C8H4O9
Molar mass	244.11 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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	Infobox references

In chemistry, furantetracarboxylic acid is an organic compound with formula C
₈H
₄O
₉, or (C₄O)(-(CO)OH)₄, which can be viewed as deriving from furan C
₄H
₄O through replacement of the four hydrogen atoms by carboxyl functional groups -(CO)OH.

By removal of four protons, the acid is expected to yield the anion C
₈O⁴⁻
₉, furantetracarboxylate, 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
₈H
₃O⁻
₉, C
₈H
₂O²⁻
₉, and C
₈HO³⁻
₉, called respectively trihydrogen-, dihydrogen-, and hydrogenfurantetracarboxylate. The same names are used for the corresponding esters.

The acid can be obtained by from dioxalylsuccinate.[1][2][3]

The salt rubidium trihydrogenfurantetracarboxylate RbH
₃C
₈O
₉ crystallizes as white needles.[4]

References

B. I. Zapadinskii, B. I. Liogon'kii, and A. A. Berlin (1973), Syntheses of Tetracarboxylic Acids. Russian Chemical Reviews, volume 42 issue 11, page 939. Online version accessed on 2010-01-03.
H.Sutter (1932), Annalen, volume 499, page 47. Cited by Zapadinskii et al.
T.Reichstein, A.Grussner, K.Schiudlerk, and E. Hardmeyer (1933), Helv.Chim.Acta, volume 16, page 276. Cited by Zapadinskii et al.
Iain C. Paul and Leslie L. Martin (1967), The crystal and molecular structure of the monorubidium salt of furantetracarboxylic acid. Acta Crystallogr. volume 22 pages 559-567 doi:10.1107/S0365110X67001136

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[zapa-1] B. I. Zapadinskii, B. I. Liogon'kii, and A. A. Berlin (1973), Syntheses of Tetracarboxylic Acids. Russian Chemical Reviews, volume 42 issue 11, page 939. Online version accessed on 2010-01-03.

[nef1887-2] H.Sutter (1932), Annalen, volume 499, page 47. Cited by Zapadinskii et al.

[nef1890-3] T.Reichstein, A.Grussner, K.Schiudlerk, and E. Hardmeyer (1933), Helv.Chim.Acta, volume 16, page 276. Cited by Zapadinskii et al.

[paul-4] Iain C. Paul and Leslie L. Martin (1967), The crystal and molecular structure of the monorubidium salt of furantetracarboxylic acid. Acta Crystallogr. volume 22 pages 559-567 doi:10.1107/S0365110X67001136

Furantetracarboxylic acid

See also

References