Acetylferrocene
Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COMe). It consists of ferrocene substituted by an acetyl group on one of the cyclopentadienyl rings. It is an orange, air-stable solid that is soluble in organic solvents.
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Names | |
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Other names
Acetylferrocene | |
Identifiers | |
3D model (JSmol) |
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ECHA InfoCard | 100.013.676 |
PubChem CID |
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RTECS number |
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Properties | |
[Fe(C5H4COCH3)(C5H5)] | |
Molar mass | 228.07 g/mol |
Appearance | Red brown crystal |
Density | 1.014 g/mL |
Melting point | 81 to 83 °C (178 to 181 °F; 354 to 356 K) [1] |
Boiling point | 161 to 163 °C (322 to 325 °F; 434 to 436 K) (4 mmHg) |
Insoluble in water, soluble in most organic solvents | |
Hazards | |
GHS pictograms | ![]() |
GHS Signal word | Danger |
GHS hazard statements |
H300 |
P264, P301+310 | |
NFPA 704 (fire diamond) | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
25 mg kg−1 (oral, rat) 50 mg kg−1 (oral, mouse)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Infobox references | |
Preparation and reactions
Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride (Ac2O):
- Fe(C5H5)2 + Ac2O → (C5H5)Fe(C5H4Ac) + HOAc
The experiment is often conducted in the instructional laboratory to illustrate acylation as well as chromatographic separations.[3][4]
Acetylferrocene can be converted to many derivatives, e.g., reduction to the chiral alcohol (C5H5)Fe(C5H4CH(OH)Me) and precursor to vinylferrocene. The oxidized derivative, acetylferrocenium, is used as a 1e-oxidant in the research laboratory.[5]
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References
- Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.
- http://msds.chem.ox.ac.uk/AC/acetylferrocene.html
- Bozak, R. E. "Acetylation of ferrocene: A chromatography experiment for elementary organic laboratory" J. Chem. Educ., 1966, volume 43, p 73.doi:10.1021/ed043p73
- 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
External links
Media related to Acetylferrocene at Wikimedia Commons
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