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453048 Sigma-Aldrich

Dichlorobis(tri-o-tolylphosphine)palladium(II)

97%

Synonym: PdCl2[P(o-Tol)3]2

  • CAS Number 40691-33-6

  • Linear Formula [(CH3C6H4)3P]2PdCl2

  • Molecular Weight 786.06

  •  MDL number MFCD00274659

  •  PubChem Substance ID 24868751

  •  NACRES NA.22

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Homogeneous Pd Catalysts, Palladium Catalysts
Quality Level   200
assay   97%
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
core: palladium
mp   280 °C (dec.) (lit.)
storage temp.   room temp
SMILES string   Cl[Pd]Cl.Cc1ccccc1P(c2ccccc2C)c3ccccc3C.Cc4ccccc4P(c5ccccc5C)c6ccccc6C
InChI   1S/2C21H21P.2ClH.Pd/c2*1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;;;/h2*4-15H,1-3H3;2*1H;/q;;;;+2/p-2
InChI key   OTYPIDNRISCWQY-UHFFFAOYSA-L

Description

General description

Dichlorobis(tri-o-tolylphosphine)palladium(II) is a useful catalyst for C-C and C-N coupling reactions.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Catalyst for C-C and C-N coupling reaction.

Dichlorobis(tri-o-tolylphosphine)palladium(II) has been employed as catalyst for the following studies:
• Reaction of tributyltin enolates, prepared in situ from tributyltin methoxide and enol acetates, with aryl bromides.
• Coupling reaction of aryl bromides with vinylic acetates.
• Negishi-Reformatsky coupling reaction of aryl bromides with ethyl 2-(tributylstannyl)acetates.
• Synthesis of (E)-methyl 3-(7-indolyl)-2-methacrylate, via Heck reaction.
• Synthesis of imidazopyrimidine derivatives.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
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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