Acetylferrocene

Acetylferrocene
Names
	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) [1]
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 pictograms
GHS Signal word	Danger
GHS hazard statements	H300
GHS precautionary statements	P264, P301+310
NFPA 704 (fire diamond)	1 4 0
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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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	Infobox references

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.

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
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

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

[2] ttp://msds.chem.ox.ac.uk/AC/acetylferrocene.html

[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