ChemicalBook CAS DataBase List Ferrocene

Ferrocene synthesis

5synthesis methods

Product Name:Ferrocene
CAS Number:102-54-5
Molecular formula:C10H10Fe
Molecular Weight:186.03

Dicyclopentadienyliron may be obtained in a single-step synthetic route by heating cyclopentadiene with iron or iron pentacarbonyl at 300°C:
2C₅H₅ + Fe → (C₅H₅)₂Fe
Also, it can be prepared by the reaction of iron(II) chloride with cyclopentadiene in the presence of an alkyl amine or a similar base.
Another convenient method of preparing this π-complex of iron is a twostep process in which the first step involves preparation of cyclopentadienyl Grignard reagent, such as 2,4-cyclopentadienylmagnesium bromide C5H5MgBr which may then be combined with ferric chloride to yield dicyclopentadienyl iron:
3C₅H₅MgBr + FeCl₃ → (C₅H₅)₂Fe + 3MgBrCl
Another general method of preparation involves the reaction of cyclopentadiene with sodium metal or sodium hydride in tetrahydrofuran (THF). Addition of iron(II) chloride to this solution forms the complex dicyclopentadienyliron:
2C₅H₆ + 2Na → 2C₅H₅ˉ + 2Na+ + H₂
In 3:2 molar ratio of cyclopentadiene to sodium cyclopentene is obtained along with cyclopentadienidide (C₅H₅ˉ ) anion:
3C₅H₆ + 2Na → 2C5H5¯ + 2Na+ + C₅H₈
FeCl₂ + 2C5H₆Na → (C5H5)₂Fe + 2NaCl

7705-08-0
422 suppliers
$9.00/1g

542-92-7
91 suppliers
inquiry

102-54-5
436 suppliers
$5.00/25g

Yield:102-54-5 85%

Reaction Conditions:

with diethylamine in 1,2-dimethoxyethane;diethylamine;amine method; FeCl3:C5H6=1.3;;

References:

Pruett, R. L.;Morehouse, E. L. [Advances in Chemistry Series,1959,vol. 23,p. 368 - 371] [Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A1, 2.1.1.2, page 16 - 18]

1282-37-7
16 suppliers
$135.00/5g

102-54-5
436 suppliers
$5.00/25g

References

7705-08-0
422 suppliers
$9.00/1g

102-54-5
436 suppliers
$5.00/25g

References

Ferrocene, [(2-pyridinylmethoxy)carbonyl]- (9CI)

348161-12-6
0 suppliers
inquiry

102-54-5
436 suppliers
$5.00/25g

References

12125-80-3 Synthesis

12125-80-3
1 suppliers
inquiry

102-54-5
436 suppliers
$5.00/25g

References

Ferrocene Related Search:

Ferrocenecarboxaldehyde Ferrocenemethanol Chromocene (S)-(+)-3-Hydroxytetrahydrofuran 3-Hydroxytetrahydrofuran Ferrocenecarboxylic acid Acetylferrocene 1,1'-Bis(diphenylphosphino)ferrocene [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)