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SMILES string
COc1c(P(C2CCCCC2)C3CCCCC3)c(c4c(C(C)C)cc(C(C)C)cc4C(C)C)c(OC)cc1, COc1c(P(C2CCCCC2)C3CCCCC3)c(c4c(C(C)C)cc(C(C)C)cc4C(C)C)c(OC)cc1
InChI
1S/C35H53O2P/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28/h19-25,27-28H,9-18H2,1-8H3, 1S/C35H53O2P/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28/h19-25,27-28H,9-18H2,1-8H3
InChI key
WDVGNXKCFBOKDF-UHFFFAOYSA-N, WDVGNXKCFBOKDF-UHFFFAOYSA-N
product line
ISOM8™
assay
(HPLC), ≥98%
form
solid
mol wt
536.77
reaction suitability
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, reaction type: Fluorinations, reagent type: ligand
mp
191-194 °C (Lit.), 187-195 °C
application(s)
diagnostic assay manufacturing
life science and biopharma
functional group
phosphine
greener alternative category
storage temp.
room temp
Quality Level
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Application
Notable characteristics & key uses:
- Steric & Electronic Properties: Its bulky biaryl structure ensures stability, selectivity, and reduced side reactions, while the electron-deficient phosphine group boosts catalytic reactivity.
- Metal Binding: Excellent for palladium and nickel-catalyzed processes like Suzuki and Buchwald-Hartwig reactions, stabilizing the metal center for improved efficiency.
- Catalyst Stability: Enhances longevity and prevents degradation, delivering higher yields and cost-effectiveness under challenging conditions.
- Versatility: Works across various solvents, temperatures, and reaction conditions, making it ideal for diverse synthetic processes.
- Cross-Coupling Reactions: Promotes efficient carbon-carbon bond formation with minimal by-products in Suzuki, Heck, and Sonogashira reactions.
- Diverse Substrate Compatibility: Performs well with challenging functional groups, enabling versatile synthetic pathways.
- Enhanced Reaction Conditions: Allows for milder, eco-friendly reaction conditions.
- Scalability: Suitable for both small-scale labs and large-scale industrial applications, ensuring consistent results.
Pd-Catalyzed C–N Coupling via Buchwald–Hartwig amination using BrettPhos ligand: This study demonstrates the scalabilityand efficiency of BrettPhos in palladium-catalyzed C–N bond formation, enablingselective coupling under mild conditions suitable for the synthesis of complexmolecules on a larger scale. (Seb Caille et al., 2015).
Pd-Catalyzed Denitrative Cyanation of Nitroarenes with BrettPhos Ligand: This study highlights the denitrative cyanation of nitroarenes using amino acetonitriles. The method efficiently converts nitroarenes into aryl nitriles, offering a halogen- and metal-waste-free catalytic process suitable for large-scale applications (Junichiro Yamaguchi et al., 2024).
Incorporating BrettPhos into your synthetic strategies enhances efficiency, reliability, and innovation, offering robust support for research applications while ensurin gseamless scalability for manufacturing.
Features and Benefits
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 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 “Waste Prevention”, “Atom Economy” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard
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