Ferrocene

Organometallic compound: Fe(II) sandwiched between two cyclopentadienyl rings / From Wikipedia, the free encyclopedia

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Ferrocene is an organometallic compound with the formula Fe(C5H5)2. The molecule is a complex consisting of two cyclopentadienyl rings bound to 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.[8]

Quick facts: Names, Identifiers, Properties, Structure, Ha...
Ferrocene
Names
Preferred IUPAC name
Ferrocene[1]
Other names
  • Dicyclopentadienyl iron
  • Bis(η5-cyclopentadienyl)iron
  • Iron(II) cyclopentadienide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.764
UNII
  • InChI=1S/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2 Y
    Key: KTWOOEGAPBSYNW-UHFFFAOYSA-N Y
  • 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
C10H10Fe
Molar mass 186.04 g/mol
Appearance light orange powder
Odor camphor-like
Density 1.107 g/cm3 (0 °C), 1.490 g/cm3 (20 °C)[2]
Melting point 172.5 °C (342.5 °F; 445.6 K)[3]
Boiling point 249 °C (480 °F; 522 K)
Insoluble in water, soluble in most organic solvents
log P 2.04050 [4]
Structure
D5d / D5h / D5
Metallocene
No Permanent Dipole moment due to rapid Cp rotations[5]
Hazards
NFPA 704 (fire diamond)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)[7]
REL (Recommended)
TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[7]
IDLH (Immediate danger)
N.D.[7]
Related compounds
Related compounds
cobaltocene, nickelocene, chromocene, ruthenocene, osmocene, 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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The rapid growth of organometallic chemistry is often attributed to the excitement arising from the discovery of ferrocene and its many analogues, such as metallocenes.