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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:
12161600
PubChem Substance ID:
24894802
NACRES:
NA.22

vapor pressure

0.03 mmHg ( 40 °C)

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.

Signal Word

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 Code

4.1B - Flammable solid hazardous materials

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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CMK-5 mesoporous carbon synthesized via chemical vapor deposition of ferrocene as catalyst support for methanol oxidation
Lei Z, et al.
The Journal of Physical Chemistry C, 3(112), 722-731 (2008)
Asymmetric catalysis with chiral ferrocene ligands
Dai LX, et al.
Accounts of Chemical Research, 36(9), 659-667 (2003)
Augustus W Lang et al.
ChemSusChem, 11(5), 854-863 (2018-02-02)
Transparent wood composites, with their high strength and toughness, thermal insulation, and excellent transmissivity, offer a route to replace glass for diffusely transmitting windows. Here, conjugated-polymer-based electrochromic devices (ECDs) that switch on-demand are demonstrated using transparent wood coated with poly(3,4-ethylenedioxythiophene):poly(styrene
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
The syntheses and catalytic applications of unsymmetrical ferrocene ligands
Atkinson RCJ, et al.
Chemical Society Reviews, 33(33), 313-328 (2004)
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