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349585

Sigma-Aldrich

Benzoylferrocene

≥98%

Synonym(s):

Ferrecenophenone, Ferrocenyl phenyl ketone, Ferrocenyl(phenyl)methanone, NSC 54800, (Benzoylcyclopentadienyl)cyclopentadienyliron

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About This Item

Empirical Formula (Hill Notation):
C17H14FeO
CAS Number:
1272-44-2
Molecular Weight:
290.14
EC Number:
215-054-2
MDL number:
MFCD00001431
UNSPSC Code:
12352300
PubChem Substance ID:
24861687
NACRES:
NA.22

assay

≥98%

reaction suitability

core: iron
reagent type: catalyst

mp

105-107 °C (lit.)

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.O=C([C]2[CH][CH][CH][CH]2)c3ccccc3

InChI

1S/C12H9O.C5H5.Fe/c13-12(11-8-4-5-9-11)10-6-2-1-3-7-10;1-2-4-5-3-1;/h1-9H;1-5H;

InChI key

JJHHJZCYDPLHIL-UHFFFAOYSA-N

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Application

Reactant for:
  • Deprotonative metalation of ferrocenes[1]
  • Oxidative chemistry[2]
  • Reduction of ferrocenyl ketones[3]
  • Polymerization of C-ferrocenyl-substituted phosphaalkene[4]

Reactant for synthesis of:
  • Planat chiral triferrocenylmethane derivative[5]
  • Chiral ferrocenyl alcohols via asymmetric transfer hydrogenation[6]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
14108TI
S33658
S33004
14217DI
14010KN

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Yong Leng Kelvin Tan et al.
Dalton transactions (Cambridge, England : 2003), 48(48), 10871-10881 (2009-12-22)
A series of compounds is described in which one of the ethyl groups in diethylstilbestrol has been replaced by a ferrocenyl substituent. Only those derivatives incorporating phenol moieties underwent isomerisation from the Z to the E form, and some of
Gandrath Dayaker et al.
Chemical communications (Cambridge, England), 46(16), 2862-2864 (2010-04-07)
A mixed lithium-cadmium amide and a combination of lithium and zinc amides were reacted with a range of ferrocenes; deprotonative mono- or dimetallation in general occurred chemoselectively at room temperature, as evidenced by subsequent quenching with iodine.
H. Zhang and Z. Bian,
Journal of Organometallic Chemistry, 692, 5687-5689 (2007)
J. R. Garabatos-Perera and H. Butenschoen,
Journal of Organometallic Chemistry, 694, 2047-2052 (2009)
Y. Wu, et al.,
Tetrahedron Asymmetry, 20, 584-587 (2009)
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