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V697230

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

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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
MDL number:
MFCD00015757
UNSPSC Code:
12352300
PubChem Substance ID:
329761901
NACRES:
NA.22

Quality Level

100

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

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

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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

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Description
Pricing

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
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)
Paul A Allegretti et al.
Bioorganic & medicinal chemistry, 28(1), 115193-115193 (2019-11-24)
Small molecule stimulation of β-cell regeneration has emerged as a promising therapeutic strategy for diabetes. Although chemical inhibition of dual specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A) is sufficient to enhance β-cell replication, current lead compounds have inadequate cellular potency for in
Star?Shaped Oligothiophenes for Solution?Processible Organic Field?Effect Transistors.
Ponomarenko S, et al.
Advances in Functional Materials, 13(8), 591-596 (2003)
Shunsuke Chiba et al.
Journal of the American Chemical Society, 131(36), 12886-12887 (2009-08-25)
A Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via an unprecedented C-C bond cleavage-C-N bond formation sequence, providing substituted azaheterocycles.
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