Chemical Properties
crystalline solid
Uses
Ferrocenecarboxaldehyde, is used to prepare chiral ferrocene aziridinylmethanols for selective azomethine ylide cycloaddtion. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals.
reaction suitability
core: iron
reagent type: catalyst
Synthesis
Ferrocenecarboxaldehyde can be obtained from the reaction of ferrocene and N-methylformylaniline in phosphorus trichloride, treated with sodium bicarbonate. The product can also be obtained after a similar step with N,N-dimethylformamide involved in the reaction.
Purification Methods
It forms red crystals from heptane/CH2Cl2, EtOH or pet ether and sublimes at 70o/1mm. The cyanohydrin has m 104o (from *C6H6/EtOH). The semicarbazone has m 217-219o(dec) after recrystallisation from aqueous EtOH. The oxime provides two isomers from pet ether viz m 96-99o and m 155o. The O-acetyloxime has m 80-81o after recrystallisation from hexane [Lindsay & Hauser J Org Chem 22 355 1957]. The 2,4-dinitrophenylhydrazone has m 248o(dec). [Beilstein 16 IV 1798, Graham et al. J Am Chem Soc 79 3416 1957, Broadhead et al. J Chem Soc 650 1958.]
