349585

Sigma-Aldrich

Benzoylferrocene

≥98%

Synonym(s):
NSC 54800, Ferrocenyl(phenyl)methanone, (Benzoylcyclopentadienyl)cyclopentadienyliron, Ferrocenyl phenyl ketone, Ferrecenophenone
Empirical Formula (Hill Notation):
C17H14FeO
CAS Number:
Molecular Weight:
290.14
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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
  • Oxidative chemistry
  • Reduction of ferrocenyl ketones
  • Polymerization of C-ferrocenyl-substituted phosphaalkene

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

Packaging

5 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Kevin J T Noonan et al.
Chemical communications (Cambridge, England), 35(35), 3658-3660 (2007-08-31)
The addition polymerization of a ferrocenyl-substituted P[double bond]C bond leads to new redox-active polymers with functional ferrocene and phosphine moieties.
H. Zhang and Z. Bian,
Journal of Organometallic Chemistry, 692, 5687-5689 (2007)
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.
Y. Wu, et al.,
Tetrahedron Asymmetry, 20, 584-587 (2009)
J. R. Garabatos-Perera and H. Butenschoen,
Journal of Organometallic Chemistry, 694, 2047-2052 (2009)

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