Furantetracarboxylic acid

Furantetracarboxylic acid
Names
	Preferred IUPAC name Furantetracarboxylic acid
Identifiers
CAS Number	20416-04-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	207476;
PubChem CID	237617;
UNII	526V46EZC7 ;
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). verify (what is ?) 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

[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

[1]

[2]

[3]

[4]

Furantetracarboxylic acid

See also

References