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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.699
EC Number
  • 215-068-9
  • InChI=1S/2C6H5O2.Fe/c2*7-6(8)5-3-1-2-4-5;/h2*1-4H,(H,7,8);
    Key: ISVVAJYTLASNEJ-UHFFFAOYSA-N
  • [CH]1[CH][CH][C]([CH]1)C(=O)O.[CH]1[CH][CH][C]([CH]1)C(=O)O.[Fe]
Properties
C12H10FeO4
Molar mass 274.053 g·mol−1
Appearance yellow solid
Density 1.769 g/cm3[1]
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
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]

References

  1. Takusagawa, F.; Koetzle, T. F. (1979). "The crystal and molecular structure of 1,1'-ferrocenedicarboxylic acid (Triclinic modification): Neutron and X-ray diffraction studies at 78 K and 298 K". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 35 (12): 2888–2896. doi:10.1107/S0567740879010906. hdl:1808/17822.
  2. "C&L Inventory". echa.europa.eu. Retrieved 14 October 2022.
  3. Petrov, Alex R.; Jess, Kristof; Freytag, Matthias; Jones, Peter G.; Tamm, Matthias (2013). "Large-Scale Preparation of 1,1′-Ferrocenedicarboxylic Acid, a Key Compound for the Synthesis of 1,1′-Disubstituted Ferrocene Derivatives". Organometallics. 32 (20): 5946–5954. doi:10.1021/om4004972.
  4. Donley, Carrie; Dunphy, Darren; Paine, David; Carter, Chet; Nebesny, Ken; Lee, Paul; Alloway, Dana; Armstrong, Neal R. (2002). "Characterization of Indium−Tin Oxide Interfaces Using X-ray Photoelectron Spectroscopy and Redox Processes of a Chemisorbed Probe Molecule: Effect of Surface Pretreatment Conditions". Langmuir. 18 (2): 450–457. doi:10.1021/la011101t.
  5. Orlowski, G. A.; Kraatz, H. B. (2006). "Peptide Films on Surfaces: Preparation and Electron Transfer". Metal-Containing and Metallosupramolecular Polymers and Materials. ACS Symposium Series. Vol. 928. pp. 392–400. doi:10.1021/bk-2006-0928.ch027. ISBN 9780841239296.
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