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919780

Sigma-Aldrich

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

Synonym(s):

Pd(dppf)Cl2

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About This Item

Linear Formula:
(C17H14P)2Fe . PdCl2
CAS Number:
72287-26-4
UNSPSC Code:
12352103
NACRES:
NA.22

form

solid

Quality Level

100

composition

~ 4 wt.% loading of catalyst

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

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;;/q2*-1;;;2*+2/p-2

InChI key

NXQGGXCHGDYOHB-UHFFFAOYSA-L

Application

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.

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

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For larger scale uses, product also available in powdered form (697230) & (931217)

Other Notes

High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads

Versatile Methods to Dispense Sub-Milligram Quantities of Solids using Chemical Coated Beads for High-Throughput Experimentation

ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H350i

Hazard Classifications

Carc. 1B Inhalation

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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)
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)
Star−Shaped Oligothiophenes for Solution−Processible Organic Field-Effect Transistors
Ponomarenko S A, et al.
Advances in Functional Materials, 13(8), 591-596 (2003)
Sho Fujii et al.
Physical chemistry chemical physics : PCCP, 19(42), 28943-28949 (2017-10-24)
A novel sensor, 4-[2-(9-anthryl)ethynyl]-1,10-phenanthroline (1), exhibits highly intense fluorescent in the wavelength region of 440-600 nm (maximum wavelength (λf) = 470 nm) with the quantum yield (Φf) and lifetime (τf) being 0.90 and 4.2 ns, respectively, in CH3CN at 298
Versatile Methods to Dispense Sub-Milligram Quantities of Solids using Chemical Coated Beads for High-Throughput Experimentation.
Martin C M, et al.
Organic Process Research & Development, 23(9), 1900-1907 (2019)
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