Acetylferrocene

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.

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

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]