Acetylferrocene

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Acetylferrocene
Names
IUPAC name
1-Ferrocenylethan-1-one[1]
Other names
Acetylferrocene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.676 Edit this at Wikidata
EC Number
  • 215-043-2
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)[2]
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 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):
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).
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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.[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

External links

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