Acetylferrocene

Acetylferrocene
Acetylferrocene
Names
Other names
Acetylferrocene
Identifiers
1271-55-2 YesY
ECHA InfoCard 100.013.676
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
T+
R-phrases R24, R28
S-phrases (S1), S28, S36/37/39, S48[2]
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
4
0
Lethal dose or concentration (LD, LC):
25 mg kg−1 (oral, rat)
50 mg kg−1 (oral, mouse)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references
This crystal of acetylferrocene was grown as part of an undergraduate course in UCL’s Department of Chemistry.

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.

Preparation and reactions

Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride. The complete preparation from aromatization of dicyclopentadiene to ferrocene is:

The experiment is often conducted in the instructional laboratory to illustrate acylation as well as chromatographic separations.[4][5]

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.[6]

References

  1. ↑ Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.
  2. ↑ https://fscimage.fishersci.com/msds/69220.htm
  3. ↑ http://msds.chem.ox.ac.uk/AC/acetylferrocene.html
  4. ↑ 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
  5. ↑ 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
  6. ↑ 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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