177261

Sigma-Aldrich

DPPF

greener alternative

97%

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

Quality Level

assay

97%

reaction suitability

reagent type: catalyst
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

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.

Packaging

1, 10, 25 g in glass bottle

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Tanimori, Shinji; et al.
Synthesis, 5, 865-869 (2006)
Wolfe, J. P.; Buchwald, S. L.
Journal of the American Chemical Society, 119, 6054-6054 (1997)
Lera et al.
Organic letters, 2(24), 3873-3875 (2000-12-02)
A method for the palladium-catalyzed synthesis of alkynylphosphonates from 1,1-dibromo-1-alkenes has been developed. In general, the best catalyst system for this transformation was found to be Pd(OAc)(2), dppf, H-phosphonate, propylene oxide, DMF, 80 degrees C. The reaction appears tolerant of...
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)

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