928364

XPhos ChemBeads

• Synonym(s): 2-Dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl
• Empirical Formula (Hill Notation): C₃₃H₄₉P
• CAS Number: 564483-18-7
• Molecular Weight: 476.72
• MDL number: MFCD04117682
• UNSPSC Code: 12352103
• NACRES: NA.82

Properties

• assay: ~6 wt.% loading of catalyst
• Quality Level: 100
• form: solid
• reaction suitability: reagent type: catalyst; reaction type: Cross Couplings
• extent of labeling: ~6 wt. % loading of catalyst
• InChI: 1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3
• InChI key: UGOMMVLRQDMAQQ-UHFFFAOYSA-N

Description

General description

XPhos [2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable electron-rich biaryl monophosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

For larger scale uses, product also available in powdered form (638064)

Application

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

• Preparation of functionalized benzylic sulfones via palladium-catalyzed Negishi cross-coupling between alkyl sulfones and aryl halides.
• Along with pre-milled palladium(II) acetate as a pre-catalyst for the Stille cross-coupling of aryl chlorides with tributylarylstannanes to form the corresponding biaryl compounds.
• Along with platinum chloride to catalyze the hydrosilylation of terminal arylalkynes with silanes to form functionalized β-(E)-vinylsilanes.
• Ligand used in a Pd-catalyzed Suzuki coupling leading to C-15 analogs of vindoline.Direct annulation of 2-haloanilines to indoles and tryptophans catalyzed by Pd. Synthesis of regioregular polythiophenes.
  
  ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

Learn more about ChemBeads products

Other Notes

High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads

Versatile Methods to Dispense Sub-Milligram Quantities of Solids using Chemical Coated Beads for High-Throughput Experimentation

ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H350i
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 1B Inhalation
• Storage Class: 6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• wgk_germany: WGK 3