Insoluble in water, soluble in most organic solvents
log P
2.04050[3]
Structure
Point group
D5h(eclipsed) D5d(staggered)
Molecular shape
Sandwich structure with iron centre
Hazards
NFPA 704 (fire diamond)
[6]
3
2
1
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)[5]
REL (Recommended)
TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[5]
IDLH (Immediate danger)
N.D.[5]
Related compounds
Related compounds
Metallocene
f-block metallocene
Actinocene
Thorocene
Protactinocene
Uranocene
Neptunocene
Plutonocene
Zirconocene
Vanadocene
Chromocene
Bis(benzene)chromium
Manganocene
Nickelocene
Cobaltocene
Ruthenocene
Rhodocene
Osmocene
Hassocene
Stannocene
Plumbocene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound
Ferrocene is an organometallic compound with the formula Fe(C5H5)2. The molecule is a complex consisting of two cyclopentadienyl rings sandwiching a central iron atom. It is an orange solid with a camphor-like odor that sublimes above room temperature, and is soluble in most organic solvents. It is remarkable for its stability: it is unaffected by air, water, strong bases, and can be heated to 400 °C without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium cation Fe(C5H5)+2.[7] Ferrocene and the ferrocenium cation are sometimes abbreviated as Fc and Fc+ respectively.
The first reported synthesis of ferrocene was in 1951. Its unusual stability puzzled chemists, and required the development of new theory to explain its formation and bonding. The discovery of ferrocene and its many analogues, known as metallocenes, sparked excitement and led to a rapid growth in the discipline of organometallic chemistry. Geoffrey Wilkinson and Ernst Otto Fischer, both of whom worked on elucidating the structure of ferrocene, later shared the 1973 Nobel Prize in Chemistry for their work on organometallic sandwich compounds. Ferrocene itself has no large-scale applications, but has found more niche uses in catalysis, as a fuel additive, and as a tool in undergraduate education.
^International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1041. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^"Ferrocene (102-54-5)". ChemicalBook. Retrieved 3 February 2010.
^"FERROCENE Material safety data sheet". ChemSrc.
^Lide DR, ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. p. 3.258. ISBN 0-8493-0486-5.
^ abcNIOSH Pocket Guide to Chemical Hazards. "#0205". National Institute for Occupational Safety and Health (NIOSH).
^"Ferrocene MSDS". ScienceLab. Archived from the original on 2015-12-12. Retrieved 2015-11-25.
^Cite error: The named reference werner2012 was invoked but never defined (see the help page).
Ferrocene is an organometallic compound with the formula Fe(C5H5)2. The molecule is a complex consisting of two cyclopentadienyl rings sandwiching a central...
above. A QRE with ferrocene or another internal standard, such as cobaltocene or decamethylferrocene, referenced back to ferrocene is ideal for nonaqueous...
Dunitz, Orgel, and Rich described the structure of the "sandwich complex" ferrocene by X-ray crystallography where an iron atom is "sandwiched" between two...
a staggered conformation. The first metallocene to be classified was ferrocene, and was discovered simultaneously in 1951 by Kealy and Pauson, and Miller...
Compounds Ferrocene is an archetypal organoiron complex. It is an air-stable, sublimable compound. Cobaltocene is a structural analogue of ferrocene, but is...
Ferrocenophanes, also called ansa ferrocenes (from ansa: handle in greek), are organometallic compounds which are derived from ferrocene. They are a subset of ansa-metallocenes...
slightly above room temperature. Cobaltocene was discovered shortly after ferrocene, the first metallocene. Due to the ease with which it reacts with oxygen...
anions (Cp*−, (CH3)5C−5). It can also be viewed as a derivative of ferrocene, with a methyl group replacing each hydrogen atom of its cyclopentadienyl...
+7. Iron also forms many coordination compounds; some of them, such as ferrocene, ferrioxalate, and Prussian blue have substantial industrial, medical...
to the discovery of ferrocene, a very stable compound which foreshadowed the synthesis of many related sandwich compounds. Ferrocene is formed by reaction...
neighboring metal iron forms an air-stable, low-spin derivative in the form of ferrocene (Fe(C5H5)2). When conducted under an atmosphere of carbon monoxide, reduction...
organoiron compound with the formula (C5H5)Fe(C5H4COCH3). It consists of ferrocene substituted by an acetyl group on one of the cyclopentadienyl rings. It...
do this, a compound called ferrocene was used, which dyed the oil red. The fuel oil coloured by the addition of ferrocene became unsuitable for use as...
is the simplest carboxylic acid derivative of ferrocene. It can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed...
bound the metal centre; or, in organometallic compounds, such as the ferrocene [Fe(C2H5)2], where two cyclopentadienyl anions are bound to the FeII centre...
reaction. Illustrative are the conversions of benzene to acetophenone and ferrocene to acetylferrocene: (C5H5)2Fe + (CH3CO)2O → (C5H5)Fe(C5H4COCH3) + CH3CO2H...
oxidizing agents, and the reduced product, ferrocene, is inert and readily separated from ionic products. The ferrocene–ferrocenium couple is often used as a...
the structure for ferrocene as postulated by Pauson and Keally. Shortly thereafter, he published the structural data of ferrocene and the new complexes...
D. Dunitz, L. E. Orgel and R. A. Rich, who confirmed the structure of ferrocene by X-ray crystallography. The correct structure, in which the molecule...
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