Acetylferrocene

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Acetylferrocene
Names
IUPAC name
Acetylferrocene
Other names
Acetylferrocene
Identifiers
3D model (
JSmol
)
ECHA InfoCard
 100.013.676 Edit this at Wikidata
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 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)[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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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

ferrocenium, 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. doi:10.1021/ed043p73
  4. doi:10.1021/ed300544n
  5. doi:10.1021/cr940053x

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Acetylferrocene&oldid=1171111662"