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412740 Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

Synonym: Dichlorobis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) dichloride, PdCl2(PPh3)2

  • CAS Number 13965-03-2

  • Linear Formula [(C6H5)3P]2PdCl2

  • Molecular Weight 701.90

  •  Beilstein/REAXYS Number 4935975

  •  EC Number 237-744-2

  •  MDL number MFCD00009593

  •  PubChem Substance ID 24865821

  •  NACRES NA.22

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Properties

Related Categories Catalysis, Catalysis and Inorganic Chemistry, Chemical Synthesis, Development Quantities for Research, Homogeneous Pd Catalysts,
Quality Level   200
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  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
  reagent type: catalyst
SMILES string   Cl[Pd]Cl.c1ccc(cc1)P(c2ccccc2)c3ccccc3.c4ccc(cc4)P(c5ccccc5)c6ccccc6
InChI   1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2
InChI key   YNHIGQDRGKUECZ-UHFFFAOYSA-L

Description

General description

Bis(triphenylphosphine)palladium(II) dichloride is an organometallic complex. It is an efficient cross-coupling catalyst for C-C coupling reaction, such as Negishi coupling, Suzuki coupling, Sonogashira coupling and Heck coupling reaction. Detection of bis(triphenylphosphine)palladium(II) dichloride by electrospray ionization quadrupole ion trap mass spectrometry using different imidazolium salts as the charge carrier has been reported. It is employed as catalyst for the Heck reaction medium.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Bis(triphenylphosphine)palladium(II) dichloride was employed in the following studies:
• As model catalyst for the evaluation of functionalized silica′s for the adsorptive recovery of homogeneous catalysts, via its interaction with metal centre.
• As catalyst in the synthesis of diphenylacetylene.
• One-pot synthesis of furoquinolines, via Pd-catalyzed Sonogashira coupling followed by Cu(I) catalyzed ring closure.
• Catalyst for Sonogashira coupling of aryl alkynes to 2-bromothiazole and 2-bromothiophene.

Packaging

1, 5, 25, 250 g in glass bottle

250 mg in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Catalysts
Protocols & Articles

Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

Transition-Metal Catalysts

A variety of transition-metal catalysts for the Suzuki coupling reaction are now available in our catalog. The majority of these catalysts are palladium- and nickelbased, typically utilizing phosphin...
ChemFiles Volume 1 Article 1
Keywords: Coupling reactions, Ligands, Suzuki coupling

Related Content

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Palladium catalyzed cross-coupling reactions have revolutionized the way in which molecules are constructed. From the fields of organic synthesis and medicinal chemistry, to materials science and pol...
Keywords: Catalysis, Coupling reactions, Cross couplings, Materials Science, Medicinal chemistry, Organic synthesis, Polymer science, transformation

Peer-Reviewed Papers
15

References

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