The Melting Point of Ferrocene

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The melting point of ferrocene can be determined using an electric refractometer. You should compare your results to those reported in the literature.

Inorganic, orange solid that sublimes above room temperature (powders vaporize readily). Soluble in organic solvents.

It is a highly aromatic compound and has an odor reminiscent of camphor. It is used in the synthesis of pharmaceuticals and agrochemicals.

Other cyclopentadienyl derivatives of ferrocene are also widely used as ligands in transition-metal catalyzed reactions. Some of these ligands are particularly useful for palladium coupling reactions. Among them is 1,1′-bis(diphenylphosphino)ferrocene, which is a valuable ligand for palladium-catalyzed alkylation of propargyl alcohols.

Many structurally unusual ferrocenyl ligands have been prepared, including the penta(ferrocenyl)cyclopentadienyl ligand which features a cyclopentadienyl anion derivatised with five ferrocene substituents.

Another cyclopentadienyl substituted ferrocene is decamethylferrocene, which is a highly oxidized form that can be used to calibrate redox potentials. It is also a good internal standard for non-aqueous electrochemistry.

Cycloidal ferrocenyl phosphines are also very versatile compounds and can be used as heterogeneous catalysts. In addition to being a good ligand for palladium-catalyzed reactions, they are useful for a variety of other metal-catalyzed regiochemical transformations.

A common undergraduate experiment involves the Friedel-Crafts reaction of ferrocene with acetic anhydride and phosphoric acid in a polar ethereal solvent. The ferrocene should be heated to about 173-174 oC before heating the acetic anhydride. Afterward, the reaction can be monitored by TLC. To make the mixture, combine 0.4 g of ferrocene and 2 mL of acetic anhydride in a test tube.

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