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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:
Molecular Weight:
554.38
MDL number:
UNSPSC Code:
12350000
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

sustainability

Greener Alternative Product

mp

181-182 °C (dec.) (lit.)

functional group

phosphine

greener alternative category

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wolfe, J. P.; Buchwald, S. L.
Journal of the American Chemical Society, 119, 6054-6054 (1997)
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
Tanimori, Shinji; et al.
Synthesis, 5, 865-869 (2006)
Driver, M. S.; Hartwig, J. F.
Journal of the American Chemical Society, 118, 7217-7217 (1996)

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