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Ferrocene, a compound of iron centered around two cyclopentadienyl rings, is an organometallic with the formula Fe(C5H5)2. It is a orange solid with a camphor-like odor that sublimes at temperatures above 100 °C. It is soluble in dilute nitric acid, concentrated sulfuric acid, benzene, petroleum ether, and tetrahydrofuran. However, it is insoluble in aqueous solutions of sodium hydroxide and phosphoric acid.
The molecule has very low boiling and melting points and can be used as an internal standard in non-aqueous electrochemistry. It can be oxidised by adding electron withdrawing groups such as carboxylic acids to shift the potential in the anodic direction, or by adding electron releasing groups such as methyl groups to make it more cathodic. It is a useful internal standard for calibration of redox potentials. It is also an important reagent in the manufacture of organic chemicals such as polyaniline and polythiophenes, as well as in semiconductor manufacturing.
Its reactivity led to the development of the field of organometallic chemistry. It reacts in a large number of reactions with alkyl halides, carboxylic acids, chloroalkyl hydride, alcohols, and ketones. It can be oxidised to form the ferrocenium cation by one-electron oxidation, or reduced to the carboxylic acid anion by treatment with magnesium metal and nitric acid.
It is a highly active ligand for electrophilic substitution reactions, undergoing acylation, alkylation, formylation, and sulfonation reactions. It is also susceptible to oxidative scission reactions, which can be mechanically triggered by strong electric fields.
