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Topic summary

Ferrocene

Ferrocene
Names Preferred IUPAC name
Ferrocene
Other names
  • Dicyclopentadienyl iron
  • Bis(η-cyclopentadienyl)iron
  • Iron(II) cyclopentadienide
Identifiers
ChEBI
ChemSpider
ECHA InfoCard100.002.764
UNII
UN number1325
  • InChI=1S/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2
    Key: KTWOOEGAPBSYNW-UHFFFAOYSA-N
  • InChI=1/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2
    Key: KTWOOEGAPBSYNW-UHFFFAOYAZ
  • [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]
Properties Fe(C5H5)2Molar mass186.035 g·mol Appearance light orange powder Odorcamphor-like Density
  • 1.107 g/cm (0 °C (32 °F; 273 K))
  • 1.490 g/cm (20 °C (68 °F; 293 K))
Melting point172.5 °C (342.5 °F; 445.6 K) Boiling point249 °C (480 °F; 522 K) 0.0001 g/L (20 °C (68 °F; 293 K)) Solubility in ethanolsoluble Solubility in benzenesoluble Solubility in diethyl ethersoluble Solubility in nitric acidsoluble (in dilute) log P3.711 (22 °C (72 °F; 295 K)) Vapor pressure
  • 1 Pa (0.00015 psi) (25.00 °C; 77.00 °F (298.15 K))
  • 7.5 Pa (0.0011 psi) (47 °C; 116 °F (320 K))
  • 80 Pa (0.012 psi) (77 °C; 170 °F (350 K))
  • 1 kPa (0.15 psi) (117 °C; 242 °F (390 K)
  • 12.3 kPa (1.8 psi) (167 °C; 332 °F (440 K))
Structure
  • D5h (eclipsed)
  • D5d (staggered)
Sandwich structure with iron centre Hazards GHS labelling: DangerH228, H302+H332, H360, H373, H401, H410P201, P202, P210, P240, P241, P260, P264, P270, P271, P273, P280, P301+P312+P330, P304+P340+P312, P308+P313, P370+P378, P391, P405, P501NFPA 704 (fire diamond)
2
2
0
10 mg/m (TWA) Lethal dose or concentration (LD, LC):
  • 1320 mg/kg (oral, rat)
  • >3000 mg/kg (dermal, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
  • TWA 15 mg/m (total)
  • TWA 5 mg/m (resp)
REL (Recommended)
  • TWA 10 mg/m (total)
  • TWA 5 mg/m (resp)
IDLH (Immediate danger)
N.D. Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ferrocene is an organometallic compound with the formula Fe(C5H5)2. The molecule is a cyclopentadienyl 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, or strong bases, and can be heated to 400 °C (752 °F) without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium cationFe(C5H5)+2.

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 structural 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, as an internal standard in electrochemical research, and as a tool in undergraduate education.

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