Ferrocene

Details:

Ferrocene is an organometallic compound with the formula Fe(C5H5)2. It is the prototypical metallocene, a type of organometallicchemical compound consisting of two cyclopentadienyl rings bound on opposite sides of a central metal atom. Such organometallic compounds are also known as sandwich compounds. The rapid growth of organometallic chemistry is often attributed to the excitement arising from the discovery of ferrocene and its many analogues.

The structure of ferrocene was confirmed by NMR spectroscopy and X-ray crystallography. Its distinctive "sandwich" structure led to an explosion of interest in compounds of d-block metals with hydrocarbons, and invigorated the development of the flourishing study of organometallic chemistry. In 1973 Fischer of the Technische Universität München and Wilkinson of Imperial College London shared a Nobel Prize for their work on metallocenes and other aspects of organometallic chemistry.
Reactions
With electrophiles
Ferrocene undergoes many reactions characteristic of aromatic compounds, enabling the preparation of substituted derivatives. A common undergraduate experiment is theFriedel-Crafts reaction of ferrocene with acetic anhydride (or acetyl chloride) in the presence of phosphoric acid as a catalyst.
Important reactions of ferrocene with electrophiles and other reagents.
Lithiation[edFerrocene reacts readily with butyl lithium to give 1,1'-dilithioferrocene, which in turn is a versatile nucleophile. But reaction of Ferrocene with t-BuLi produces monolithioferrocene only. These approaches are especially useful methods to introduce main group functionality, e.g. using S8, chlorophosphines, chlorosilanes. The strained compounds undergo ring-opening polymerization.
Fuel additives
Ferrocene and its derivatives are antiknock agents used in the fuel for petrol engines; they are safer than tetraethyllead, previously used. It is possible to buy at Halfords in the UK, a petrol additive solution which contains ferrocene which can be added to unleaded petrol to enable it to be used in vintage cars which were designed to run on leaded petrol.The iron-containing deposits formed from ferrocene can form a conductive coating on the spark plug surfaces.
Pharmaceutical
Some ferrocenium salts exhibit anticancer activity, and an experimental drug has been reported which is a ferrocenyl version of tamoxifen. The idea is that the tamoxifen will bind to the estrogen binding sites, resulting in a cytotoxicity effect.
Materials chemistry
Ferrocene, being readily decomposed to iron nanoparticles, can be used as a catalyst for the production of carbon nanotubes. The vinyl ferrocene from ferrocene can be made by a Wittig reaction of the aldehyde, a phosphonium salt and sodium hydroxide. The vinyl ferrocene can be converted into a polymer which can be thought of as a ferrocenyl version of polystyrene (the phenyl groups are replaced with ferrocenyl groups).

【Name】
Ferrocene
【CAS】
102-54-5
【Synonyms】
BIS(CYCLOPENTADIEN)IRON
BIS(CYCLOPENTADIENYL)IRON
BIS(CYCLOPENTADIENYL)IRON(+2)
di-2,4-cyclopentadien-1-yliron
DICYCLOPENTADIENYLIRON
DICYCLOPENTADIENYLIRON(II)
FERROCENE
IRON DICYCLOPENTADIENYL
Bis(eta-cyclopentadienyl) iron
biscyclopentadienyliron[qr]
Di(pi-cyclopentadienyl)iron
di-2,4-cyclopentadien-1-yliron[qr]
dicyclopentadienyl
dicyclopentadienyliron[qr]
di-pi-cyclopentadienyliron[qr]
Ferrotsen
【EINECS】
203-039-3
【Molecular Formula】
C10H10Fe
【Molecular Weight】
186.03
【Appearance】
solid
【mp 】
172-174 °C(lit.)
【bp 】
249 °C(lit.)
【vapor pressure 】
0.03 mm Hg ( 40 °C)
【Fp 】
100°C
【storage temp. 】
Flammables area
【Stability:】
Stable at room temperature. Incompatible with strong oxidizing agents. Highly flammable.
【Sensitive 】
Air & Moisture Sensitive
【Sublimation 】
100 ºC
【HS Code 】
29310095
【Usage 】
Mainly as fuel combustion additives in a variety of fuels, such as diesel, gasoline, kerosene and coal, adding a certain amount of ferrocene, it can save energy,reduce smoke and improving the efficiency. The product is very beneficial on improving low-octane gasoline, adding 1000PPm ferrocene in straight-run gasoline with only 56 octane , the octane number increased to 70. In addition, ferrocene can be used as photolysis plastic photosensitizer, polymerization initiator and ammonia synthesis catalyst.