1,1'-Ferrocenedicarboxylic acid

1,1'-Ferrocenedicarboxylic acid is the organoiron compound with the formula Fe(C₅H₄CO₂H)₂. It is the simplest dicarboxylic acid derivative of ferrocene. It is a yellow solid that is soluble in aqueous base. The 1,1' part of its name refers to the location of the carboxylic acid groups on separate rings.

1,1'-Ferrocenedicarboxylic acid

Names
IUPAC name 1,1'-Ferrocenedicarboxylic acid
Identifiers
CAS Number	1293-87-4
3D model (JSmol)	Interactive image
ChemSpider	198591
ECHA InfoCard	100.013.699
EC Number	215-068-9
PubChem CID	16211180
CompTox Dashboard (EPA)	DTXSID40926371
InChI InChI=1S/2C6H5O2.Fe/c2*7-6(8)5-3-1-2-4-5;/h2*1-4H,(H,7,8); Key: ISVVAJYTLASNEJ-UHFFFAOYSA-N
SMILES [CH]1[CH][CH][C]([CH]1)C(=O)O.[CH]1[CH][CH][C]([CH]1)C(=O)O.[Fe]
Properties
Chemical formula	C12H10FeO4
Molar mass	274.053 g·mol−1
Appearance	yellow solid
Density	1.769 g/cm3[1]
Hazards
GHS labelling:[2]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Related compounds
Related compounds	Ferrocenecarboxylic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It can be prepared by hydrolysis of its diesters Fe(C₅H₄CO₂R)₂ (R = Me, Et), which in turn are obtained by treatment of ferrous chloride with the sodium salt of the carboxyester of cyclopentadienide (C₅H₄CO₂R)⁻. Ferrocenedicarboxylic acid is the precursor to many derivatives such as the diacid chloride, the diisocyanate, the diamide, and diamine, respectively, Fe(C₅H₄COCl)₂, Fe(C₅H₄NCO)₂, Fe(C₅H₄CONH₂)₂, and Fe(C₅H₄NH₂)₂.^[3]

Derivatives of ferrocenedicarboxylic acid are components of some redox switches and redox active coatings.^[4][5]

Related compounds

• Ferrocenecarboxylic acid