Girish Mahajan (Editor)

Acetylferrocene

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Formula
  
[Fe(C5H4COCH3)(C5H5)]

Boiling point
  
161 °C

Molar mass
  
228.07 g/mol

Appearance
  
Red brown crystal

Acetylferrocene Acetylferrocene127155213CNMR

Friedel crafts acylation isolation of ferrocene acetylferrocene diacetylferrocene



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.

Contents

Acetylferrocene Acetylferrocene CAS 1271552 814518

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.

Acetylferrocene Acetylferrocene12715521HNMR

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.

Acetylferrocene wwwsigmaaldrichcomcontentdamsigmaaldrichstr

Acetylferrocene Acetylferrocene C12H12FeO ChemSpider

References

Acetylferrocene Wikipedia
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