Chemistry:1,1'-Ferrocenedicarboxylic acid
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| Names | |
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| IUPAC name
1,1'-Ferrocenedicarboxylic acid
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| EC Number |
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PubChem CID
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| Properties | |
| C12H10FeO4 | |
| Molar mass | 274.053 g·mol−1 |
| Appearance | yellow solid |
| Density | 1.769 g/cm3[1] |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| Related compounds | |
Related compounds
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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(C
5H
4CO
2H)
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(C
5H
4CO
2R)
2 (R = Me, Et), which in turn are obtained by treatment of ferrous chloride with the sodium salt of the carboxyester of cyclopentadienide (C
5H
4CO
2R)−
. Ferrocenedicarboxylic acid is the precursor to many derivatives such as the diacid chloride, the diisocyanate, the diamide, and diamine, respectively, Fe(C
5H
4COCl)
2, Fe(C
5H
4NCO)
2, Fe(C
5H
4CONH
2)
2, and Fe(C
5H
4NH
2)
2.[3]
Derivatives of ferrocenedicarboxylic acid are components of some redox switches and redox active coatings.[4][5]
Related compounds
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.
- ↑ "C&L Inventory". https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/70456.
- ↑ 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. 928. pp. 392–400. doi:10.1021/bk-2006-0928.ch027. ISBN 9780841239296.
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