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716146

Sigma-Aldrich

[FeCl2bis(dppbz)]

95%

Synonym(s):

1,2-Phenylenebis[diphenyl]phosphine iron complex, FeCl2(dppbz)2

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About This Item

Empirical Formula (Hill Notation):
C60H48Cl2FeP4
CAS Number:
101566-80-7
Molecular Weight:
1019.67
MDL number:
MFCD16621441
UNSPSC Code:
12352300
PubChem Substance ID:
329763369

Assay

95%

reaction suitability

core: iron
reagent type: catalyst

mp

228-236 °C

SMILES string

Cl[Fe]Cl.c1ccc(cc1)P(c2ccccc2)c3ccccc3P(c4ccccc4)c5ccccc5.c6ccc(cc6)P(c7ccccc7)c8ccccc8P(c9ccccc9)c%10ccccc%10

InChI

1S/2C30H24P2.2ClH.Fe/c2*1-5-15-25(16-6-1)31(26-17-7-2-8-18-26)29-23-13-14-24-30(29)32(27-19-9-3-10-20-27)28-21-11-4-12-22-28;;;/h2*1-24H;2*1H;/q;;;;+2/p-2

InChI key

LSSVPSLVWGKHSR-UHFFFAOYSA-L

Application

Catalyst for Negishi coupling and Suzuki coupling.
Catalyst for:
  • Negishi coupling of alkyl halides with arylaluminum reagents
  • Fluoroaromatic coupling reactions
  • Negishi coupling of benzyl halides and phosphates

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
24796JK

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Robin B Bedford et al.
Chemical communications (Cambridge, England), (5), 600-602 (2009-03-14)
Iron-based catalysts containing either 1,2-bis(diphenylphosphino)benzene or 1,3-bis(diphenylphosphino)propane give excellent activity and good selectivity in the Negishi coupling of aryl zinc reagents with a range of benzyl halides and phosphates.
Takuji Hatakeyama et al.
Chemical communications (Cambridge, England), (10), 1216-1218 (2009-02-26)
A catalytic amount of 1,2-bis(diphenylphosphino)benzene (DPPBz) achieves selective cleavage of sp(3)-carbon-halogen bond in the iron-catalysed cross-coupling between polyfluorinated arylzinc reagents and alkyl halides, which was unachievable with a stoichiometric modifier such as TMEDA; the selective iron-catalysed fluoroaromatic coupling provides easy
Shintaro Kawamura et al.
Chemical communications (Cambridge, England), 46(33), 6054-6056 (2010-07-27)
The first example of an iron-catalysed Negishi coupling between arylaluminium reagents and alkyl halides illustrates that the co-existing salts highly influence the dynamic equilibrium of the organoaluminium species, and have a critical effect on the reactivity and selectivity of the
Robin B Bedford et al.
Chemical communications (Cambridge, England), (42), 6430-6432 (2009-10-21)
Employing co-catalytic zinc reagents facilitates the iron-catalysed Suzuki cross-coupling of tetraarylborates with both benzyl and 2-heteroaryl halides.

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