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Ferrocene is an organometallic chemical compound with the formula Fe(C5H5)2. It is the prototypical metallocene, a class of organic compounds that are characterized by two cyclopentadienyl rings bound on opposite sides to a central transition metal atom. This structure is often called a “sandwich compound” because of its similarity to the structure of benzene. It was the first example of this type of organometallic compound and is one of the most important catalysts in modern organic synthesis.
It is an orange solid that has a camphor-like odor and sublimes above room temperature, but is soluble in most organic solvents. It is a highly effective reducing agent and forms a wide variety of substituted derivatives, some of which are useful as catalysts for polymerization reactions and inorganic synthesis. It is also an excellent choice for the preparation of chiral molecules.
Its high boiling point makes it a convenient internal standard for electrochemical work in non-aqueous media and can be used to calibrate other electrodes. It is frequently employed as a reference electrode in cyclic voltammetry. The name ferrocene is derived from the combination of the words ferro and cene, meaning iron benzene.
X-ray crystallography shows that ferrocene is a flat, plane, regular pentagon with the iron atom “sandwiched” between the two cyclopentadienyl ligands. The cyclopentadienyl carbon atoms have elongated C-Fe bond lengths and alternating dihedral angles indicative of steric crowding. Ferrocene is also a bridging compound, which allows the formation of complexes with tetrahydrofurane or tetrahydrocinnamate.