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.

Quick facts Names, Identifiers ...

1,1'-Ferrocenedicarboxylic acid

Names
Preferred IUPAC name Ferrocene-1,1′-dicarboxylic 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 Â°C [77 Â°F], 100 kPa). Infobox references

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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]