Acetylferrocene

Acetylferrocene

Names
IUPAC name 1-Ferrocenylethan-1-one [1]
Other names Acetylferrocene
Identifiers
CAS Number	1271-55-2  Y
3D model (JSmol)	Interactive image
ChemSpider	21241939
ECHA InfoCard	100.013.676
EC Number	215-043-2
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
SMILES 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) [2]
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
Signal word	Danger
Hazard statements	H300
Precautionary statements	P264, P301+P310
NFPA 704 (fire diamond)	4 1 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). Y  verify  (what is  YN ?) Infobox references

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. ^{[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. "Brief Guide to Inorganic Nomenclature".
2. Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.
3. http://msds.chem.ox.ac.uk/AC/acetylferrocene.html ^{[ dead link ]}
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, Neil G.; Geiger, William E. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews. 96 (2): 877–910. doi:10.1021/cr940053x. PMID   11848774.

External links

• Media related to Acetylferrocene at Wikimedia Commons