PMC2000

2-(Dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl

≥98%, ISOM8^™

• Synonym(e): BrettPhos
• Empirische Formel (Hill-System): C₃₅H₅₃O₂P
• CAS-Nummer: 1070663-78-3
• Molekulargewicht: 536.77
• UNSPSC Code: 12352128
• PubChem Substance ID: 329763602
• NACRES: NA.22
• MDL number: MFCD11973797

Eigenschaften

• Quality Segment: 300
• 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
• greener alternative product score: old score: 8; new score: 1; Find out more about DOZN™ Scoring
• greener alternative product characteristics: Waste Prevention; Atom Economy; Design for Energy Efficiency; Learn more about the Principles of Green Chemistry.
• sustainability: Sustainability features
• mp: 191-194 °C (Lit.), 187-195 °C
• application(s): diagnostic assay manufacturing; life science and biopharma
• functional group: phosphine
• storage temp.: room temp
• SMILES string: 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
• InChI key: WDVGNXKCFBOKDF-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 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

Application

• Buchwald Phosphine Ligands for chemical Synthesis
• Common applications

BrettPhos, developed by the Buchwald group, is a highly effective dialkylbiaryl phosphine ligand that enhances transition metal-catalyzed reactions with unique steric and electronic properties.

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.

Recent Studies and Innovations:

1. Recyclable Pd(acac)₂/BrettPhos/PEG-1000 System for Suzuki-Miyaura Coupling: This study presents a sustainable catalytic system for nitroarenes, emphasizing its efficiency, recyclability, and greener approach to C–C bond formation. (Mingzhong Cai et al., 2024).
2. 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).
3. 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.

Buchwald Phosphine Ligands for chemical Synthesis

Legal Information

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

ISOM8 is a trademark of Sigma-Aldrich Co. LLC

Sicherheitshinweise

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