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Other names Acetylferrocene | |
Identifiers | |
CAS Number | |
ECHA InfoCard | 100.013.676 |
Properties | |
Chemical formula | |
Molar mass | 228.07 g/mol |
Appearance | Red brown crystal |
Melting point | 81–83 °C |
Boiling point | 161–163 °C (4 mmHg) |
Solubility in water | Insoluble in water, soluble in most organic solvents |
Hazards | |
NFPA 704 (fire diamond) | 4 1 0 |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 25 mg kg (oral, rat) 50 mg kg (oral, mouse) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references |
Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COMe). It consists of ferrocene substituted by one acetyl group on one of the cyclopentadienyl rings. It is an orange, air-stable solid that is soluble in organic solvents.
Preparation and reactions
Acetylferrocene is prepared by acetylation of ferrocene, usually with acetic anhydride]]:
- (C5H52)Fe + Ac2O → (C5H5)Fe(C5H4Ac) + AcOH
The experiment is often used in the instructional laboratory to illustrate acylation as well as chromatographic separations.
Acetylferrocene can be converted to many derivatives, including reduction to the chiral alcohol. The oxidized derivative, acetylferrocenium, is used as a 1e-oxidant in the research laboratory.
References
- Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.
- http://msds.chem.ox.ac.uk/AC/acetylferrocene.html
- https://fscimage.fishersci.com/msds/69220.htm
- Donahue, C. J., Donahue, E. R., "Beyond Acetylferrocene: The Synthesis and NMR Spectra of a Series of Alkanoylferrocene Derivatives", Journal of Chemical Education 2013, volume 90, pp. 1688. doi:10.1021/ed300544n
- Connelly, N. G., Geiger, W. E., "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877. doi:10.1021/cr940053x