Acetylferrocene

Acetylferrocene
Names
	IUPAC name Acetylferrocene
	Other names Acetylferrocene
Identifiers
CAS Number	1271-55-2 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.013.676
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)
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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[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

^ Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.
^ http://msds.chem.ox.ac.uk/AC/acetylferrocene.html ^{[dead link]}
^ 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
^ 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
^ Connelly, N. G., Geiger, W. E., "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877. doi:10.1021/cr940053x

External links

Media related to Acetylferrocene at Wikimedia Commons

[sigma-1] Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.

[2] ttp://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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