PMC2005

tBuXPhos

≥98%, ISOM8^™

• Synonim(y): tBuXPhos, 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, t-Bu XPhos, tert-Butyl XPhos, 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, t-Bu XPhos, tert-Butyl XPhos
• Wzór empiryczny (zapis Hilla): C₂₉H₄₅P
• Numer CAS: 564483-19-8
• Masa cząsteczkowa: 424.64
• UNSPSC Code: 12352128
• MDL number: MFCD06411306
• NACRES: NA.21
• eCl@ss: 32151101

Właściwości

• Quality Segment: 300
• product line: ISOM8^™
• assay: ≥98%
• form: solid
• purified by: HPLC
• reaction suitability: reaction type: Arylations, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Carboxylations, reaction type: Cross Couplings, reaction type: Decarboxylations, reagent type: ligand
• greener alternative product score: old score: 12; new score: 1; Find out more about DOZN™ Scoring
• sustainability: Sustainability features
• mp: 144-145 °C (Lit.), 148-151 °C (lit.)
• application(s): diagnostic assay manufacturing; life science and biopharma
• functional group: phosphine
• storage temp.: room temp
• SMILES string: 1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3, CC(P(C(C=CC=C1)=C1C(C(C(C)C)=CC(C(C)C)=C2)=C2C(C)C)C(C)(C)C)(C)C
• InChI: 1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3
• InChI key: SACNIGZYDTUHKB-UHFFFAOYSA-N

Opis

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 for chemical Synthesis


Common applications


tBuXPhos, a phosphine ligand developed by the Buchwald group, significantly enhances palladium-catalyzed cross-coupling reactions for forming C-C, C-N, and C-O bonds, making it an invaluable tool in synthetic chemistry. Integration of t-BuXPhos into synthetic methodologies improves reaction efficiency, selectivity, and reliability while supporting both research-scale investigations and scalable manufacturing processes.


Notable characteristics & key uses:

• Steric Effects: Thebulky tert-butyl substituents provide favorable steric hindrance that stabilizes palladium intermediates and enhances reaction selectivity by controlling substrate approach and coordination.
• Electronic Properties: Tunable electronic characteristics allow for optimizationof palladium catalyst reactivity and selectivity across different reaction conditions and substrate types.
• Stability: Exhibitsexcellent thermal and chemical stability, enabling efficient catalysis duringprolonged reactions at elevated temperatures without ligand degradation. Many tBuXPhos-palladium complexes also demonstrate good air stability, facilitating handling and use under ambient conditions without requiring strictly inert atmospheres.
• Cross-Coupling Reactions: t-BuXPhos plays a crucial role in Suzuki-Miyaura, Stille, and other palladium-catalyzed cross-coupling reactions for efficient carbon-carbon bond formation.
• Asymmetric Synthesis: tBuXPhos when used with chiral variants or in chiral catalyst systems, enables asymmetric synthesis to produce enantiomerically enriched compounds with high selectivity.
• C-H Activation: Facilitates direct functionalization of C-H bonds in hydrocarbons, enabling site-selective transformations without pre-functionalization.
• AminationReactions: Enables efficient palladium-catalyzed amination of arylhalides and related substrates, providing direct access to aromatic amines andrelated nitrogen-containing compounds.

Recent Studies and Innovations:

Green and Sustainable Cross-Coupling with tBuXPhos : tBuXPhos enables highly efficient Heck-Cassar-Sonogashira reactions in sodium stearate surfactant-mediated aqueous systems, achieving up to 98% isolated yields atroom temperature. This protocol eliminates toxic solvents, operates under mild conditions (RT to 40°C), and scales from milligrams to kilograms. The method enables synthesis of pharmaceutically relevant compounds while maintaining environmental sustainability. (KinjalMarkana et al., 2025).


tBuXPhos forEco-Friendly Mechanochemical Synthesis:tBuXPhos demonstrates exceptional performance in mechanochemical Pd-catalyzed cross-coupling of in-situ generated Reformatsky Zn-enolates with aryl halides, delivering 91% NMR yields alongside CPhos and XPhos. The ligand enables efficient α-arylated ester and amide synthesis under ambient air conditions without zinc pre-activation, achieving up to 95% yields with commercially affordablearyl bromides. This method eliminates strong basic conditions and inert atmosphere requirements, supporting sustainable mechanochemical transformations. (Tomáš Čarný et al., 2025).

Legal Information

Usage subject to Patents: EP 1097158; JP 5758844; CA 2336691

ISOM8 is a trademark of Sigma-Aldrich Co. LLC

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

Ta strona może zawierać tekst przetłumaczony maszynowo.

Informacja o środkach bezpieczeństwa

• Klasa składowania: 11 - Combustible Solids
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable