Ferrocenecarboxylic acid is a metal-organic compound characterized by connecting two ferrocene molecules through a carboxy ligand. Notably, ferrocene is a stable yet highly reactive metal-organic compound that has been extensively researched due to its potential applications in catalysis, materials science, and medicine. It serves as a catalyst in catalysis, facilitating the synthesis of diverse compounds through polymerization, oxidation, and reduction reactions. In materials science, it acts as a fundamental molecular building block for synthesizing polymers and nanomaterials. Although the precise mechanism of action of Ferrocenecarboxylic acid remains fully elucidated, it is believed that the carboxy ligand binds to the ferrocene molecules, forming a stable complex. This complex, in turn, engages with other molecules, including proteins, to facilitate various reactions[1-2].
Ferrocenecarboxylic acid is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
It crystallises as yellow crystals from pet ether (m 225-230odec), CHCl3 (m 208.5odec), toluene/pet ether (m 195-205odec), or aqueous ethanol. [Matsue et al. J Am Chem Soc 107 3411 1985.] The acid chloride m 49o crystallises from pentane, and has max at 458nm [Lau & Hart J Org Chem 24 280 1959]. The methyl ester crystallises from aqueous MeOH with m 70-71o. The anhydride has m 143-145o when recrystallised from pet ether [Acton & Silverstein J Org Chem 24 1487 1959]. The amide has m 168-170o when crystallised from CHCl3/Et2O or m 167-169o when crystallised from *C6H6/MeOH. [Arimoto & Haven J Am Chem Soc 77 6295 1955, Benkeser et al. J Am Chem Soc 76 4025 1954.] [Beilstein 16 IV 1807.]
[1] C. Pess?a, L. Kubota, Y. Gushikem. “Ferrocenecarboxylic acid adsorbed on Nb2O5 film grafted on a SiO2 surface: NADH oxidation study.” Electrochimica Acta 46 1 (2001): 2499–2505.
[2] H. Tsukube, S. Shinoda, H. Fukui. “Synergistic binding and chirality sensing of unprotected amino acids with ferrocenecarboxylic acid–crown ether conjugate.” Tetrahedron Letters 42 1 (2001): 7583–7585.
