PMC2003

2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl

≥98%, ISOM8^™

• Synonym(e): RuPhos
• Empirische Formel (Hill-System): C₃₀H₄₃O₂P
• CAS-Nummer: 787618-22-8
• Molekulargewicht: 466.64
• UNSPSC Code: 12352128
• NACRES: NA.22
• PubChem Substance ID: 24884189
• MDL number: MFCD06798294
• eCl@ss: 32151101

Eigenschaften

• product line: ISOM8^™
• Quality Segment: 300
• assay: (HPLC), ≥98%
• form: solid
• reaction suitability: reaction type: Arylations, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: C-X Bond Formation, reaction type: Cross Couplings, reaction type: Fluorinations
• greener alternative product score: old score: 3; new score: 1; Find out more about DOZN™ Scoring
• sustainability: Sustainability features
• mp: 123-126 °C
• application(s): diagnostic assay manufacturing
• functional group: phosphine
• storage temp.: room temp
• 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

Beschreibung

General description

Welcome to our ISOM8^™ line of high-quality products available and able to scale for manufacturing. Within our ISOM8^™ team, we have expertise and documentation to support ISO 9001 industrial and non-GMP pharma production needs, as defined by our M-Clarity^™ Program

Our portfolio of ISOM8^™ products and chemistries is ever evolving to support our valued Sigma-Aldrich customers′ requirements. Please navigate to our documents section to look at dossiers and other quality documentation for this product, provided with support of our Elevate Program.

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 Feedstocks". Click here to view its DOZN scorecard.

Application

Buchwald Phosphine Ligands forchemical Synthesis

Common applications

RuPhos developed by the Buchwald group, RuPhos and its palladium precatalyst forms are notable for being air-stable, moisture-stable,and highly soluble, enabling efficient catalysis with lower catalyst loadings and shorter reaction times in organic synthesis.

Notable characteristics & key uses:

• Steric & Electronic Properties: RuPhos′s biaryl structure with 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl configuration provides stability and selectivity. Its electron-rich phosphine and isopropoxy groups enhance catalytic reactivity and substrate compatibility
• Metal Binding: Excels in palladium and nickel-catalyzed processes including Suzuki-Miyaura coupling and Buchwald-Hartwig amination. Has a smaller Tolman cone angle than BrettPhos,donating less electron density to metals.
• Catalyst Stability: RuPhos enhances catalyst longevity and prevents degradation, delivering higher yields even under demanding conditions with superior stability and solubility.
• Versatility: Performs excellently across diverse solvents, temperatures, and reaction environments. Ideal forvaried applications, including Negishi cross-couplings of hindered aryl halides.
• Cross-Coupling Reactions: RuPhos enablesefficient C-C, C-N, C-O, C-F, C-CF₃, and C-S bond formation with minimal by-products. Particularly effective with hindered substrates like cyclic secondary amines.
• Precatalyst Integration: Incorporated into stable precatalysts like RuPhos Pd G3, offering enhanced handling and improved storage stability.
• Enhanced Reaction Conditions: Facilitates milder, environmentally friendly reactions while maintaining high catalytic activity and selectivity.
• Scalability: Suited for both laboratory research and industrial manufacturing, ensuring reproducible results across different operational scales.

Recent Studies and Innovations:

Steric Hindrance Effects: The study indicates that amines with large steric hindrance or halides with electron-withdrawing groups significantly reduce activation energy barriers in RuPhos-catalyzed reactions, enhancing overall catalytic efficiency and substrate scope. (Jiaqi Tian et al., 2020)

Catalyst-Transfer Polymerization (CTP): RuPhos excels in Suzuki−Miyaura catalyst-transfer polymerization (CTP), enabling precise synthesis of conjugated polymers with controlled molecular weights and narrow polydispersity. The ligand effectively facilitates polymerization of both electron-rich (donor) and electron-deficient (acceptor) monomers. (JaehoLee et al., 2021)

Legal Information

ISOM8 is a trademark of Sigma-Aldrich Co. LLC

M-CLARITY is a trademark of Merck KGaA, Darmstadt, Germany

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable