Acetylferrocene

Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COCH3). 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.

Acetylferrocene
Names
IUPAC name
Acetylferrocene
Other names
Acetylferrocene
Identifiers
3D model (JSmol)
ECHA InfoCard 100.013.676
RTECS number
  • OB3700000
  • InChI=1S/C7H7O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-5H,1H3;1-5H;
    Key: PHMAOJNZIFULOG-UHFFFAOYSA-N
  • CC(=O)[C]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe]
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 labelling:
GHS06: Toxic
Danger
H300
P264, P301+P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
4
1
0
Lethal dose or concentration (LD, LC):
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]

References
  1. Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.
  2. http://msds.chem.ox.ac.uk/AC/acetylferrocene.html
  3. 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
  4. 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
  5. Connelly, N. G., Geiger, W. E., "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877. doi:10.1021/cr940053x
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