Misplaced Pages

1,1'-Ferrocenedicarboxylic acid

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
1,1'-Ferrocenedicarboxylic acid
Names
IUPAC name 1,1'-Ferrocenedicarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.699 Edit this at Wikidata
EC Number
  • 215-068-9
PubChem CID
CompTox Dashboard (EPA)
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
  • 1(1)C(=O)O.1(1)C(=O)O.
Properties
Chemical formula C12H10FeO4
Molar mass 274.053 g·mol
Appearance yellow solid
Density 1.769 g/cm
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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.

Derivatives of ferrocenedicarboxylic acid are components of some redox switches and redox active coatings.

Related compounds

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.
Categories: