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All Photos(5)

663131

Sigma-Aldrich

RuPhos

greener alternative

98%

Synonym(s):
2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl
Empirical Formula (Hill Notation):
C30H43O2P
CAS Number:
Molecular Weight:
466.64
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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
Find out more about DOZN™ Scoring

greener alternative product characteristics

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

impurities

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

mp

123-126 °C

functional group

phosphine

greener alternative category

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

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1 of 4

This Item
718742638072638064
RuPhos 98%

Sigma-Aldrich

663131

RuPhos

BrettPhos 98%

Sigma-Aldrich

718742

BrettPhos

SPhos 98%

Sigma-Aldrich

638072

SPhos

XPhos 98%

Sigma-Aldrich

638064

XPhos

form

solid

form

solid

form

-

form

-

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

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Fluorinations

reaction suitability

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

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: C-C Bond Formation, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Hiyama Coupling, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Sonogashira Coupling, reagent type: ligand
reaction type: Stille Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

123-126 °C

mp

187-195 °C

mp

164-166 °C (lit.)

mp

187-190 °C (lit.)

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

greener alternative product score

old score: 3
new score: 1
Find out more about DOZN™ Scoring

greener alternative product score

old score: 8
new score: 1
Find out more about DOZN™ Scoring

greener alternative product score

old score: 10
new score: 1
Find out more about DOZN™ Scoring

greener alternative product score

old score: 2
new score: 1
Find out more about DOZN™ Scoring

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

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Product Number
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25G
Pack Size/Quantity

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

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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
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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