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Sigma-Aldrich

DPPF

greener alternative

97%

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Synonym(s):
1,1′-Ferrocenediyl-bis(diphenylphosphine), dppf
Empirical Formula (Hill Notation):
C34H28FeP2
CAS Number:
12150-46-8
Molecular Weight:
554.38
MDL number:
MFCD00001422
PubChem Substance ID:
24850625
NACRES:
NA.22

Quality Level

200

Assay

97%

form

powder

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Carbonylations
reagent type: ligand
reaction type: Ene Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Tsuji-Trost Reaction

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

181-182 °C (dec.) (lit.)

functional group

phosphine

greener alternative category

Aligned,

SMILES string

[Fe].[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6

InChI

1S/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;

InChI key

HPXNTHKXCYMIJL-UHFFFAOYSA-N

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General description

Novel functionalized furan derivatives were prepared via Pd-phosphine sequential C-C and C-O bond formation.
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

Ligand for ruthenium-catalyzed greener amine synthesis from amines and alcohols by hydrogen-borrowing.

Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology
Ligand used in a Pd(II)-catalyzed cross-coupling synthesis of oxazepine ring systems.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Palucki, M.;Wolfe, J. P.; Buchwald, S.-L.
Journal of the American Chemical Society, 118, 10333-10333 (1996)
Driver, M. S.; Hartwig, J. F.
Journal of the American Chemical Society, 118, 7217-7217 (1996)
Tanimori, Shinji; et al.
Synthesis, 5, 865-869 (2006)
Anastasia, L.; Dumond, Y. R.; Negishi, E.
European Journal of Organic Chemistry, 3039-3039 (2001)
Alejandro Pérez Luna et al.
Organic letters, 5(25), 4771-4774 (2003-12-05)
The diastereoselective synthesis of hydrazinocyclopentenes 6 or 7 can be achieved in a straightforward manner from Diels-Alder adduct 4 using an acid-catalyzed rearrangement or a palladium-catalyzed allylic substitution reaction. In the latter case, enantioenriched compounds with ee values up to
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