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Merck
CN

V697230

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

powder, Vetec™

Synonym(s):

Pd(dppf)Cl2

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About This Item

Linear Formula:
(C17H14P)2Fe · PdCl2
CAS Number:
72287-26-4
Molecular Weight:
731.70
UNSPSC Code:
12352300
PubChem Substance ID:
329761901
NACRES:
NA.22
MDL number:
MFCD00015757

Key Documents

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Product Name

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), Vetec™

SMILES string

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

InChI

1S/2C17H14P.2ClH.Fe.Pd/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;2*1H;;/q;;;;;+2/p-2

InChI key

JCWIWBWXCVGEAN-UHFFFAOYSA-L

form

powder

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling

mp

266-283 °C (lit.)

storage temp.

room temp

Quality Level

100

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Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Catalyst for C-C and C-N coupling reaction.
Pd(dppf)Cl2 may be used as an effective palladium catalyst in the following reactions:

  • Cross-coupling of sec-alkyl and n-alkyl Grignard reagents with high yield and selectivity.
  • Suzuki coupling of aryl boronic esters with [11C]methyl iodide to form functionalized [11C]toluene derivatives
  • Kumada cross-coupling of 1,3,5-tribromobenzene with Grignard reagents to form star-shaped oligothiophenes
For small scale and high throughput uses, product is also available as ChemBeads (919780)

Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5893V
WXBF5183V

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An improved synthesis of substituted [11C] toluenes via Suzuki coupling with [11C] methyl iodide
Hostetler E, et al.
Journal of Labelled Compounds & Radiopharmaceuticals, 48(9), 629-634 (2005)
Dichloro [1,1?-bis (diphenylphosphino) ferrocene] palladium (II): an effective catalyst for cross-coupling reaction of a secondary alkyl grignard reagent with organic halides
Hayashi T, et al.
Tetrahedron Letters, 20(21), 1871-1874 (1979)
Star?Shaped Oligothiophenes for Solution?Processible Organic Field?Effect Transistors.
Ponomarenko S, et al.
Advances in Functional Materials, 13(8), 591-596 (2003)
Electrophilic activation of benzaldehydes through ortho palladation: one-pot synthesis of 3-methylene-indan-1-ols through a domino allylstannylation/Heck reaction under neutral conditions.
Ján Cvengros et al.
Angewandte Chemie (International ed. in English), 48(33), 6148-6151 (2009-07-11)
Andrei V Krivtsov et al.
Cancer cell, 36(6), 660-673 (2019-12-11)
Inhibition of the Menin (MEN1) and MLL (MLL1, KMT2A) interaction is a potential therapeutic strategy for MLL-rearranged (MLL-r) leukemia. Structure-based design yielded the potent, highly selective, and orally bioavailable small-molecule inhibitor VTP50469. Cell lines carrying MLL rearrangements were selectively responsive
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