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106860

Sigma-Aldrich

Acetylferrocene

95%

Synonym(s):

(Acetylcyclopentadienyl)cyclopentadienyliron, 1-Ferrocenylethanone, Acetoferrocene

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About This Item

Empirical Formula (Hill Notation):
C12H12FeO
CAS Number:
1271-55-2
Molecular Weight:
228.07
EC Number:
215-043-2
MDL number:
MFCD00001432
UNSPSC Code:
12161600
PubChem Substance ID:
24846743
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

reaction suitability

core: iridium
reagent type: catalyst

mp

81-83 °C (lit.)

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.CC(=O)[C]2[CH][CH][CH][CH]2

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;

InChI key

PHMAOJNZIFULOG-UHFFFAOYSA-N

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General description

Acetylferrocene is an organometallic compound that can be used as a catalyst and as a starting material for the synthesis of complex organometallic compounds.

Application

Acetylferrocene can be used as:
  • A Precursor to synthesize 1-ferrocenylethanol by reduction in the presence of sodium borohydride.
  • An electroactive compound along with MgO nanoparticles to modify carbon paste electrode (CPE) that can be used to determine L-cysteine.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Martin Bertau et al.
Bioorganic & medicinal chemistry, 12(11), 2973-2983 (2004-05-15)
The bioavailability of lipophilic substrates is critical for biotransformations with isolated enzymes as well as with whole cells. With the example of a series of lipophilic ketones the suitability of saccharides as potent solubilisers for highly lipophilic substrates was demonstrated.
Magnetic NiFe2O4 nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti-tumour activity
Applied Organometallic Chemistry, 30(11), 917-923 (2016)
Jing Zhang et al.
Guang pu xue yu guang pu fen xi = Guang pu, 25(10), 1568-1572 (2006-01-07)
Inclusion complex of acetylferrocene-thiosemicarbazone(TAF) with beta-cyclodextrin(beta-CD) has been prepared by using kneading method. Elemental analysis and the solubility determination proved that 1:1 inclusion complex has been formed. Characterization of the inclusion complex was studied by UV, FTIR, and X-ray diffractometry.
Thiol-Ene Chemistry of Vinylferrocene: A Simple and Versatile Access Route to Novel Electroactive Sulfur-and Ferrocene-Containing Model Compounds and Polysiloxanes
Martinez-Montero I, et al.
Macromolecules, 47(4), 1301-1315 (2014)
Ysaías J Alvarado et al.
Molecules (Basel, Switzerland), 10(2), 457-474 (2007-11-17)
The solvent effect on the position of the carbonyl vibrational stretching of acetylferrocene in aprotic media was studied in this work. The solvent-induced shifts in this organometallic compound were interpreted in terms of the alternative reaction field model(SCRF-MO) proposed by
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