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932205

Sigma-Aldrich

RuPhos ChemBeads

Synonym(s):

2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl

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About This Item

Empirical Formula (Hill Notation):
C30H43O2P
CAS Number:
Molecular Weight:
466.64
UNSPSC Code:
12352112
NACRES:
NA.22

form

solid

Quality Level

storage temp.

2-8°C

InChI

1S/C30H43O2P/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25/h11-13,18-25H,5-10,14-17H2,1-4H3

InChI key

MXFYYFVVIIWKFE-UHFFFAOYSA-N

Application

Bulky phosphine ligand used in a palladium-catalyzed cross-coupling of aminoethyltrifluoroborates with electron-poor aryl bromides.

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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Product is also available as neat precatalyst (663131)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Versatile Methods to Dispense Submilligram Quantities of Solids Using Chemical-Coated Beads for High-Throughput Experimentation
Martin, et al.
Organic Process Research & Development, 23, 1900?1907-1900?1907 (2019)
Gary A Molander et al.
Organic letters, 9(2), 203-206 (2007-01-16)
A set of phenethylamines has been successfully prepared via Suzuki-Miyaura cross-coupling of diverse potassium beta-aminoethyltrifluoroborates with aryl halides. The potassium beta-aminoethyltrifluoroborates were easily prepared via hydroboration of enamine and enamide precursors. [reaction: see text].
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand
Ruben Martin et al.
Accounts of chemical research, 41(11), 1461-1473 (2008-07-16)
The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon-carbon

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