1,1'-Ferrocenedicarboxylic acid

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/c27-6(8)5-3-1-2-4-5;/h21-4H,(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
Hazards
	GHS labelling:
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

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.

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

References

^ 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.
^ "C&L Inventory". echa.europa.eu. Retrieved 14 October 2022.
^ 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.
^ 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.
^ 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.

[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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