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655414 Sigma-Aldrich

2-(2′-Di-tert-butylphosphine)biphenylpalladium(II) acetate

97%

Synonym: Palladium, (acetato-ΚO) [2′-[bis (1,1 dimethylethyl) phosphino-ΚP] [1,1′-biphenyl]-2-yl ΚC]

  • CAS Number 577971-19-8

  • Empirical Formula (Hill Notation) C22H29O2PPd

  • Molecular Weight 462.86

  •  MDL number MFCD04117716

  •  PubChem Substance ID 24884102

  •  NACRES NA.22

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Homogeneous Pd Catalysts, Other Palladacycle Coupling Catalysts, Palladium Catalysts More...
assay   97%
reaction suitability   core: palladium
  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
mp   130-140 °C (dec.) (lit.)
storage temp.   room temp
SMILES string   CC(=O)[Pd]1c2ccccc2-c3ccccc3[PH]1(C(C)(C)C)C(C)(C)C
InChI   1S/C20H26P.C2H4O2.Pd/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16;1-2(3)4;/h7-12,14-15H,1-6H3;1H3,(H,3,4);/q;;+1/p-1
InChI key   IEYDYAASBZOBOC-UHFFFAOYSA-M

Description

General description

2-(2′-Di-tert-butylphosphine)biphenylpalladium(II) acetate is a novel, air- and moisture-and thermally stable catalyst.

Application

It can be used as a pre-catalyst for the amination of aryl chlorides. It can also be used to prepare N-methyl-6-heterocyclic-1-oxoisoindoline derivatives via Buchwald-Hartwig amination reaction of N-methyl-6- bromoisoindoline-1-one with different amines under microwave condition.

Precatalyst for Buchwald-Hartwig amination reaction.

Packaging

1 g in glass bottle

250 mg 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

Nájera Catalysts

Oxime-derived palladacycles 3 and 4 (Figure 2) introduced by Professor Carmen Nájera and co-workers at the Universidad de Alicante (Alicante, Spain) are very efficient phosphine-free precatalysts for...
Aldrich ChemFiles 2007, 7.5, 6.
Keywords: Chemfiles, Coupling reactions, Metallations, Solvents

Palladacycle Coupling Catalysts

Palladacyclic catalysts developed by Bedford’s group are examples of a select group of catalysts capable of affecting a variety of coupling reactions using difficult to activate aryl chlorides at ver...
William Sommer
ChemFiles 2007, 7.10, 17.
Keywords: Aminations, Catalysis, Coupling reactions, Ligands, Solvents, Stille coupling, Suzuki coupling

Peer-Reviewed Papers
15

References

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