Vinylferrocene
{{Chembox
| ImageFile = VinylFc.svg
| ImageSize = 122
| ImageAlt =
| IUPACName = Vinylferrocene
|SystematicName=Ethenylferrocene
| OtherNames = Ferrocenylethene
|Section1={{Chembox Identifiers
| CASNo = 1271-51-8
| PubChem = 129738036
| InChI=1S/2C7H7.2C5H5.2Fe/c2*1-2-7-5-3-4-6-7;2*1-2-4-5-3-1;;/h2*2-6H,1H2;2*1-5H;;/q4*-1;2*+2
| InChIKey = VXSUCWUFYMRJEK-UHFFFAOYSA-N
| ChemSpiderID = 24590072
| SMILES = C=C[C-]1C=CC=C1.C=C[C-]1C=CC=C1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Fe+2] }}
|Section2={{Chembox Properties
| C=12|H=12|Fe=1
| MolarMass =
| Appearance = orange solid
| Density =
| MeltingPtC = 50-52
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Vinylferrocene is the organometallic compound with the formula (C5H5)Fe(C5H4CH=CH2). It is a derivative of ferrocene, with a vinyl group attached to one cyclopentadienyl ligand. As the ferrocene analogue of styrene, it is the precursor to some polyferrocenes.{{cite journal|title= Ferrocene-mediated enzyme electrode for amperometric determination of glucose|author1=Cass, Anthony E. G. |author2=Davis, Graham |author3=Francis, Graeme D. |author4=Hill, H. Allen O. |author5=Aston, William J. |author6=Higgins, I. John |author7=Plotkin, Elliot V. |author8=Scott, Lesley D. L. |author9=Turner, Anthony P. F. |journal=Analytical Chemistry|year=1984|volume=56|issue=4 |pages=667–671|doi=10.1021/ac00268a018|pmid=6721151}} It is an orange, air-stable oily solid that is soluble in nonpolar organic solvents.
Vinylferrocene can be prepared by the dehydration of α-hydroxylethylferrocene, which is obtained from acetylferrocene.{{cite journal|title= Organometallic π-complexes. XIV. Vinylmetallocenes
|author1=Rausch, Marvin D. |author2=Siegel, Armand |journal=Journal of Organometallic Chemistry|year=1968|volume=11|pages=317–324|doi=10.1016/0022-328X(68)80054-3}} It can also be made by a Wittig reaction of ferrocenecarboxaldehyde.{{cite journal | vauthors = Liu WY, Xu QH, Ma YX, Liang YM, Dong NL, Guan DP |journal=J. Organomet. Chem.|year=2001|volume=625|pages=128–132|doi=10.1016/S0022-328X(00)00927-X|title=Solvent-free synthesis of ferrocenylethene derivatives}}