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455164 Sigma-Aldrich

Tricyclohexylphosphine solution

20 wt. % in toluene

Synonym: NSC 158657, PCy3

  • CAS Number 2622-14-2

  • Linear Formula (C6H11)3P

  • Molecular Weight 280.43

  •  Beilstein/REAXYS Number 957171

  •  MDL number MFCD00003853

  •  PubChem Substance ID 24869033

  •  NACRES NA.22

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Properties

Related Categories Basic Phosphine Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling, Phosphine Compounds,
concentration   20 wt. % in toluene
functional group   phosphine
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
SMILES string   C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
InChI   1S/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2
InChI key   WLPUWLXVBWGYMZ-UHFFFAOYSA-N

Description

Application

Catalyst for:
• Carbonylative Suzuki-coupling of benzyl halides with potassium aryltrifluoroborates
• Suzuki-Miyaura reactions of aryl sulfonates / halides with arylboronic acids
• Synthesis of an acromelic acid A analog based 11C-labeled PET tracer
• Synthesis of (-)-Exiguolide and its analogues
• Allylation of zinc enolates

Reagent used as a ligand for a range of metal-catalyzed organic transformations.

Packaging

100, 500 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
RIDADR 
UN1294 - class 3 - PG 2 - Toluene, solution
WGK Germany 
3
Flash Point(F) 
51.8 °F
Flash Point(C) 
11 °C
Protocols & Articles

Articles

A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles

In air, Pd(OAc)2 (9.1 mg, 1.141 mmol), PCy3 (22.4 mg, 1.181 mmol), and K3PO4�H2O (276 mg, 1.21 mmol) are added to a reaction vessel equipped with a stir bar. The vessel is sealed with a septum and pu...
Keywords: Chromatography, Column chromatography

Peer-Reviewed Papers
15

References

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