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Merck

663131

RuPhos

greener alternative

98%, solid

Synonym(s):

2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl

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About This Item

Empirical Formula (Hill Notation):
C30H43O2P
CAS Number:
787618-22-8
Molecular Weight:
466.64
UNSPSC Code:
12352112
PubChem Substance ID:
24884189
NACRES:
NA.22
MDL number:
MFCD06798294

Key Documents

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Product Name

RuPhos, 98%

SMILES string

CC(C)Oc1cccc(OC(C)C)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

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

assay

98%

form

solid

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Sonogashira Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

greener alternative product score

old score: 3
new score: 1
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greener alternative product characteristics

Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

impurities

1-5% Bis(2′,6′-Diisopropoxybiphenyl)cyclohexylphosphine

mp

123-126 °C

functional group

phosphine

greener alternative category

Re-engineered,

Quality Level

300

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Atom Economy”, “Design for Energy Efficiency” and “Use of Renewable Feedstock”. Click here to view its DOZN scorecard.

Application

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

For small scale and high throughput uses, product is also available as ChemBeads (932205)

Legal Information

Usage subject to Patents: EP 1097158; JP 5758844; CA 2336691

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000436168
0000436168
SHBQ9145
SHBR5715
SHBN8257

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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
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
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

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THE DOZN SCALE RuPhos (663131)

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