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671479 Sigma-Aldrich

cataCXium® A

95%

Synonym: Di(1-adamantyl)-n-butylphosphine

  • CAS Number 321921-71-5

  • Empirical Formula (Hill Notation) C24H39P

  • Molecular Weight 358.54

  •  Beilstein/REAXYS Number 8726448

  •  MDL number MFCD05861606

  •  PubChem Substance ID 329760425

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis,
Quality Level   100
assay   95%
reaction suitability   reagent type: catalyst
reaction type: Cross Couplings
  reagent type: ligand
reaction type: Arylations
  reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reagent type: ligand
reaction type: C-C Bond Formation
  reagent type: ligand
reaction type: Heck Reaction
  reagent type: ligand
reaction type: Sonogashira Coupling
  reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
functional group   phosphine
SMILES string   CCCCP([C@]12C[C@H]3C[C@H](C[C@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
InChI   1S/C24H39P/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24/h17-22H,2-16H2,1H3/t17-,18+,19-,20-,21+,22-,23-,24-
InChI key   HTJWUNNIRKDDIV-FECFBMJZSA-N

Description

General description

Sold in collaboration with Solvias AG

Application

cataCXium® A or di-adamantylalkylphosphine is a bulky and electron-rich phosphine ligand that is highly effective for palladium catalyzed cross-coupling reactions such as Heck and Suzuki coupling, Buchwald-Hartwig amination of aryl chlorides, and α-arylation reactions of ketones.

Other applications:
• palladium-catalyzed carbonylation of aryl and heteroaryl halides
• palladium-catalyzed synthesis of (hetero)aromatic nitriles
• palladium-catalyzed aminocarbonylation of aryl halides

Packaging

1, 5 g in glass bottle

Features and Benefits

• Mild reaction condition
• Low catalyst loading
• High yield and turn over number

Legal Information

US7148176

cataCXium is a registered trademark of Evonik Degussa GmbH

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

Catalysts
Protocols & Articles

Articles

cataCXium® - Ligands and Complexes for Efficient Cross-Coupling Reactions

Cross-coupling reactions are an important class of catalytic transformations with applications in polymer science as well as in the fine chemicals and pharmaceutical industries. The use of aryl chlor...
Keywords: Aminations, Buchwald-Hartwig amination, Cancer, Catalysis, Coupling reactions, Cross couplings, Industries, Ligands, Pharmaceutical, Polymer science, Suzuki coupling, transformation

cataCXium®

Cross-coupling reactions are an important class of catalytic transformations with applications in polymer science as well as in the fine chemicals and pharmaceutical industries. The use of aryl chlor...
William Sommer
ChemFiles Volume 7 Article 10
Keywords: Aminations, Applications, Buchwald-Hartwig amination, Catalysis, Coupling reactions, Cross couplings, Industries, Ligands, Pharmaceutical, Polymer science, Suzuki coupling, transformation

Related Content

cataCXium® - Ligands and Complexes for Efficient Cross-Coupling Reactions

Cross-coupling reactions are an important class of catalytic transformations with applications in polymer science as well as in the fine chemicals and pharmaceutical industries. The use of aryl chlor...
Keywords: Aminations, Applications, Buchwald-Hartwig amination, Cancer, Catalysis, Coupling reactions, Cross couplings, Industries, Ligands, Pharmaceutical, Polymer science, Suzuki coupling, transformation

Peer-Reviewed Papers
15

References

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