638080

tBuXPhos

98%

• Synonym(s): tBuXPhos, 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, t-Bu XPhos, tert-Butyl XPhos
• Empirical Formula (Hill Notation): C₂₉H₄₅P
• CAS Number: 564483-19-8
• Molecular Weight: 424.64
• MDL number: MFCD06411306
• UNSPSC Code: 12352002
• PubChem Substance ID: 24882908
• NACRES: NA.22

Properties

• assay: 98%
• form: solid
• reaction suitability: reaction type: Cross Couplings; reagent type: ligand; reaction type: Arylations; reagent type: ligand; reaction type: Buchwald-Hartwig Cross Coupling Reaction; reagent type: ligand; reaction type: Carboxylations; reagent type: ligand; reaction type: Decarboxylations
• greener alternative product score: old score: 12; new score: 1; Find out more about DOZN™ Scoring
• greener alternative product characteristics: Atom Economy; Design for Energy Efficiency; Use of Renewable Feedstocks; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• mp: 148-151 °C (lit.)
• functional group: phosphine
• greener alternative category: Re-engineered,
• SMILES string: 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

Description

General description

tBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

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”, “Use of Renewable Feedstock” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

Learn more about Buchwald Phosphine Ligands

Application

tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr₄F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity.

tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation.
It can be used in the following reactions:

• Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
• Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
• Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)