4037. Ferrocene

Nomenclature

CAS number: 102-54-5
Dicyclopentadienyliron; biscyclopentadienyliron.
C10H10Fe; mol wt 186.03.
C 64.56%, H 5.42%, Fe 30.02%.

Description and 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).

Chemical structure

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.

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.