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526460 Sigma-Aldrich

Xantphos

97%

Synonym: 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

  • CAS Number 161265-03-8

  • Empirical Formula (Hill Notation) C39H32OP2

  • Molecular Weight 578.62

  •  MDL number MFCD00233866

  •  PubChem Substance ID 24874555

  •  NACRES NA.22

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Properties

Related Categories Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling,
Quality Level   300
assay   97%
reaction suitability   reaction type: Cross Couplings
  reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reagent type: ligand
reaction type: C-X Bond Formation
  reagent type: ligand
reaction type: Hydroformylations
  reagent type: ligand
reaction type: Miyaura Borylation Reaction
  reagent type: ligand
reaction type: Stille Coupling
  reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
mp   224-228 °C (lit.)
functional group   phosphine
SMILES string   CC1(C)c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c(cccc15)P(c6ccccc6)c7ccccc7
InChI   1S/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3
InChI key   CXNIUSPIQKWYAI-UHFFFAOYSA-N

Description

Packaging

1, 5, 25 g in glass bottle

Application

Ligand used in a synthesis of heterocycles by palladium-catalyzed C-N cross coupling of 3-bromothiophenes with 2-aminopyridines. Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols.

Metal chelating ligand for catalysis.

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

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Catalysts
Protocols & Articles

Articles

A Convenient and Expeditious Synthesis of 3-(N-Substituted) Aminocoumarins via Palladium-Catalyzed Buchwald-Hartwig Coupling Reaction

Decarboxylative coupling of sp-sp2 carbons is possible by palladium catalyst. Employing propiolic acid as a difunctional alkyne, and using the consecutive reactions of the Sonogashira reaction and th...
Keywords: Chromatography, Flash chromatography

Selective Amination of Polyhalopyridines Catalyzed by a Palladium-Xantphos Complex

Amination of 5-bromo-2-chloropyridine (1a) catalyzed by a palladium-Xantphos complex predominately gives 5-amino-2-chloropyridine product 3a in 96% isolated yield and excellent chemoselectivity (3a/4...
Keywords: Aminations, Catalysis, Chromatography, High performance liquid chromatography

Peer-Reviewed Papers
15

References

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