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808423 Sigma-Aldrich

HandaPhos

toluene solution (14 mg HandaPhos per 1 mL of toluene)

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Phosphine Compounds, Phosphine Ligands
Quality Level   100
form   liquid
transition temp   flash point 42.0 °F
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
storage temp.   2-8°C
SMILES string   COC(C=CC=C1OC)=[C@]1[C@@]2=C([P@](C(C)(C)C)[C@@H](CC3=C(C(C)C)C=C(C(C)C)C=C3C(C)C)O4)C4=CC=C2

Description

Application

HandaPhos is a monophosphine ligand. As reported by Lipshutz and coworkers, HandaPhos, in tandem with designer surfactant TPGS-750-M, allows for palladium-catalyzed cross-couplings to be performed at room temperature requiring levels of palladium lower than 1000 ppm (less than 0.1 mol %). HandaPhos can be used in cross-couplings such as Suzuki-Miyaura, Sonogashira, Buchwald-Hartwig and several other commonly used cross-coupling reactions.

Packaging

1 mL in glass bottle

Other Notes

HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature

Watch Professor Lipshutz talk about HandaPhos in this webinar:
From milligrams to kilograms: synthetic chemistry following nature′s lead

Safety & Documentation

Safety Information

RIDADR 
UN1294 - class 3 - PG 2 - Toluene

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Lipshutz Group – Products available at Aldrich from the Lipshutz Laboratory

From our library of Articles, Sigma-Aldrich presents Lipshutz Group – Products available at Aldrich from the Lipshutz Laboratory
Keywords: Addition reactions, Catalysis, Cross couplings, Environmental, Green chemistry, Ligands, Metathesis, Nucleophilic aromatic substitution, Olefin metathesis, Organic synthesis, Solvents, Substitutions

Peer-Reviewed Papers
15

References

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