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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
SMILES string
CC(C)Oc1cccc(OC(C)C)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4
InChI key
MXFYYFVVIIWKFE-UHFFFAOYSA-N
mp
123-126 °C
application(s)
diagnostic assay manufacturing
functional group
phosphine
storage temp.
room temp
product line
ISOM8™
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
Quality Level
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General description
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.
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Application
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
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
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