Acetylferrocene

Acetylferrocene
Names
IUPAC name
Acetylferrocene
Other names
Acetylferrocene
Identifiers
CAS Number
  • 1271-55-2 checkY
3D model (JSmol)
  • Interactive image
ECHA InfoCard 100.013.676 Edit this at Wikidata
PubChem CID
  • 10857189
RTECS number
  • OB3700000
InChI
  • 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
Chemical formula
 [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)
Solubility in water
 Insoluble in water, soluble in most organic solvents
Hazards
GHS labelling:
Pictograms
 GHS06: Toxic
Danger
Hazard statements
 H300
Precautionary statements
 P264, P301+P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
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
Chemical compound

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.

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 [dead link]
  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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