Ferrocene

Ferrocene

Names
Preferred IUPAC name Ferrocene[1]
Other names Dicyclopentadienyl iron Bis(η5-cyclopentadienyl)iron Iron(II) cyclopentadienide
Identifiers
CAS Number	102-54-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30672 N
ChemSpider	7329 Y
ECHA InfoCard	100.002.764
PubChem CID	11985121
UNII	U96PKG90JQ Y
CompTox Dashboard (EPA)	DTXSID9025326
InChI 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
SMILES [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]
Properties
Chemical formula	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)[4]
Boiling point	249 °C (480 °F; 522 K)
Solubility in water	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). N verify (what is YN ?) Infobox references

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.