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F408

Sigma-Aldrich

Ferrocene

98%

Synonym(s):

Bis(cyclopentadienyl)iron, Di(cyclopentadienyl)iron

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About This Item

Linear Formula:
Fe(C5H5)2
CAS Number:
102-54-5
Molecular Weight:
186.03
EC Number:
203-039-3
MDL number:
MFCD00001427
UNSPSC Code:
12352300
PubChem Substance ID:
24894802
NACRES:
NA.22

vapor pressure

0.03 mmHg ( 40 °C)

Quality Level

100

assay

98%

reaction suitability

core: iron
reagent type: catalyst

bp

249 °C (lit.)

mp

172-174 °C (lit.)

λmax

358 nm

storage temp.

2-8°C

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.[CH]2[CH][CH][CH][CH]2

InChI

1S/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;

InChI key

DFRHTHSZMBROSH-UHFFFAOYSA-N

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Application

Ferrocene (dicyclopentadienyliron) can be used:
  • As a scaffold for chiral ligands in asymmetric catalysis.
  • In ferrocene-based electrolytes for dye sensitized solar cells applications.
  • In the synthesis of unsymmetrical ferrocene ligands used as catalysts in cross-coupling, hydrogenation, allylic substitution, hydroformylation and aldol reactions.
  • In the synthesis of two-dimensional hexagonally ordered mesoporous carbon (CMK-5) via chemical vapor deposition method, which is used as a catalyst support in oxidation of methanol.
  • In the synthesis of molecular hybrids of ferrocene and fullerene (Bucky ferrocenes).
  • In the preparation of ferrocenium salt which is used as a mild oxidant.

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Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 1 - Flam. Sol. 1 - Repr. 1B - STOT RE 2 Inhalation

target_organs

Liver

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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The syntheses and catalytic applications of unsymmetrical ferrocene ligands
Atkinson RCJ, et al.
Chemical Society Reviews, 33(33), 313-328 (2004)
Muneebah Adams et al.
Dalton transactions (Cambridge, England : 2003), 42(13), 4677-4685 (2013-01-31)
A series of aryl-functionalized and ferrocenyl monothiosemicarbazone compounds (L1-L4) were synthesized in moderate yields via a general Schiff-base condensation reaction. The thiosemicarbazone (TSC) ligands were reacted with the ruthenium dimer [Ru(Ar)(μ-Cl)Cl](2) (Ar = benzene; p-cymene) to yield a series of
Sumit Kumar et al.
ACS omega, 3(9), 12106-12113 (2018-10-16)
1H-1,2,3-Triazole tethered imidazole-isatin and imidazole-isatin-thiosemicarbazone conjugates were synthesized and evaluated against MCF-7 and MDA-MB-231 cell lines. Antiproliferative activities of the synthesized conjugates revealed an optimum combination of longer alkyl chain length as spacer and a halogen-substituent on the isatin ring
Applications of ferrocenium salts in organic synthesis
Toma S and Sebesta R
Synthesis, 12(47), 1683-1695 (2015)
Hybrid of ferrocene and fullerene
Sawamura M, et al.
Journal of the American Chemical Society, 32(124), 9354-9355 (2002)
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