Ferrocene

Title: Ferrocene
CAS Registry Number: 102-54-5
Additional Names: Dicyclopentadienyliron; biscyclopentadienyliron
Molecular Formula: C10H10Fe
Molecular Weight: 186.03
Percent Composition: C 64.56%, H 5.42%, Fe 30.02%
Literature References: Prepn: Kealy, Pauson, Nature 168, 1039 (1951); Pauson, US 2680756 (1954 to Du Pont); Miller et al., J. Chem. Soc. 1952, 632; Anzilotti, Weinmayr, US 2791597 (1957 to Du Pont). Other prepn: Pruett, Morehouse in Adv. Chem. Ser. 23, entitled "Metal-Organic Compounds," M. Sittig, Ed. (ACS, Washington DC, 1959) pp 368-371; Wilkinson, Org. Synth. coll. vol. IV, 473 (1963); Cordes, FR 1341880 (1963 to BASF), C.A. 60, 6873a (1964). Structure studies: Wilkinson et al., J. Am. Chem. Soc. 74, 2125 (1952); Seibold, Sutton, J. Chem. Phys. 23, 1967 (1955). Synthesis of a helical ferrocene: T. J. Katz, J. Pesti, J. Am. Chem. Soc. 104, 346 (1982). Reviews: Rausch et al., J. Chem. Educ. 34, 268-272 (1957); M. Rosenblum, Chemistry of the Iron Group Metallocenes (John Wiley, New York, 1965) 241 pp; Bruce, Organomet. Chem. Rev. Sect. B 10, 75-122 (1972); B. W. Rockett, G. Marr, J. Organomet. Chem. 211, 215-278 (1981).
Properties: Orange needles from methanol or ethanol; odor of camphor. mp 173-174°. Sublimes above 100°. Volatile in steam. Practically insol in water, 10% NaOH, and concd boiling HCl. Sol in alcohol, ether, benzene. Dissolves in dil nitric and concd sulfuric acids forming a deep red soln with blue fluorescence. The molecule is diamagnetic and the dipole moment is effectively zero.
Melting point: mp 173-174°
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin and respiratory system. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 104.
Use: Antiknock additive for gasoline; catalyst.
Ferrocholinate Ferroglycine Sulfate Ferrosoferric Oxide Ferrous Bisglycinate Ferrous Bromide

Ferrocene
Ferrocene.svg Ferrocene-from-xtal-3D-balls.png
Ferrocene 3d model 2.png Photo of Ferrocene (powdered).JPG
Identifiers
CAS number 102-54-5 YesY
PubChem 11985121
ChemSpider 7329 YesY
UNII U96PKG90JQ YesY
ChEBI CHEBI:30672 N
Jmol-3D images Image 1
Properties
Molecular formula C10H10Fe
Molar mass 186.04 g/mol
Appearance light orange powder
Density 1.107 g/cm3 (0°C), 1.490 g/cm3 (20 °C)[1]
Melting point 172.5 °C[2]
Boiling point 249 °C
Solubility in water Insoluble in water, soluble in most organic solvents
Related compounds
Related compounds cobaltocene, nickelocene, chromocene, ruthenocene, plumbocene
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ferrocene is an organometallic compound with the formula Fe(C5H5)2. It is the prototypical metallocene, a type of organometallic chemical compound consisting of two cyclopentadienyl rings bound on opposite sides of a central metal atom. Such organometallic compounds are also known as sandwich compounds.[3][4] The rapid growth of organometallic chemistry is often attributed to the excitement arising from the discovery of ferrocene and its many analogues.