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666564 Sigma-Aldrich

N-XantPhos

97%

Synonym: 4,6-Bis(diphenylphosphino)-10H-phenoxazine, 4,6-Bis(diphenylphosphino)phenoxazine, NiXantphos

  • CAS Number 261733-18-0

  • Linear Formula (C6H3)2NHO(P(C6H5)2)2

  • Molecular Weight 551.55

  •  MDL number MFCD03788937

  •  PubChem Substance ID 24884806

  •  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   100
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: ligand
reaction type: Cross Couplings
mp   256-262 °C
functional group   phosphine
SMILES string   N1c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c1cccc5P(c6ccccc6)c7ccccc7
InChI   1S/C36H27NOP2/c1-5-15-27(16-6-1)39(28-17-7-2-8-18-28)33-25-13-23-31-35(33)38-36-32(37-31)24-14-26-34(36)40(29-19-9-3-10-20-29)30-21-11-4-12-22-30/h1-26,37H
InChI key   HSWZLYXRAOXOLL-UHFFFAOYSA-N

Description

Application

N-XantPhos is a deprotonatable chelating aryldiphosphine ligand that can be used in:
• The preparation of Pd-NiXantphos catalyst system for the room temperature cross-coupling reactions of unactivated aryl chlorides.
• The synthesis of cinchonine iridium(III) cyclometalated complex that exhibits luminescence and good quantum efficiency.
• N-XantPhos and N-modified counterparts are also used in the preparation of rhodium based catalysts for hydroformylation reaction.

Packaging

1 g in glass bottle

500 mg in glass bottle

Safety & Documentation

Safety Information

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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Protocols & Articles
Peer-Reviewed Papers
15

References

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