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Sigma-Aldrich

XPhos ChemBeads

Synonym(s):

2-Dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl

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About This Item

Empirical Formula (Hill Notation):
C33H49P
CAS Number:
Molecular Weight:
476.72
MDL number:
UNSPSC Code:
12352103

assay

~6 wt.% loading of catalyst

Quality Level

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

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.
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pictograms

Health hazard

signalword

Danger

hcodes

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

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Articles

ChemBeads, catalyst-coated glass beads, offer a simple and cost-efficient solution for dispensing miniscule amounts of solid chemical reagents for nanomole-scale use in high-throughput reaction screening.

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