PMC2011

5-(Di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazol

≥98%, ISOM8^™

• Synonym(e): BippyPhos
• Empirische Formel (Hill-System): C₃₂H₃₅N₄P
• CAS-Nummer: 894086-00-1
• Molekulargewicht: 506.62
• UNSPSC Code: 12352005
• MDL number: MFCD09038440

Eigenschaften

• product line: ISOM8^™
• Quality Segment: 300
• assay: ≥98%
• form: solid
• purified by: HPLC
• reaction suitability: reagent type: ligand, reagent type: ligand; reaction type: Amidations, reagent type: ligand; reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand; reaction type: Cross Couplings
• mp: 169-173 °C
• application(s): diagnostic assay manufacturing; life science and biopharma
• functional group: phosphine
• storage temp.: room temp
• SMILES string: CC(C)(C)P(c1ccnn1-c2c(nn(-c3ccccc3)c2-c4ccccc4)-c5ccccc5)C(C)(C)C
• InChI: 1S/C32H35N4P/c1-31(2,3)37(32(4,5)6)27-22-23-33-36(27)30-28(24-16-10-7-11-17-24)34-35(26-20-14-9-15-21-26)29(30)25-18-12-8-13-19-25/h7-23H,1-6H3
• InChI key: PTXJGGGNGMPMBG-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.

Application

The BippyPhos is a highly versatile, bulky, and electron-rich bipyrazole phosphine ligand. It excels in palladium-catalyzed cross-coupling reactions — most notably Buchwald-Hartwig amination — and is prized for its exceptional compatibility with challenging substrates, including electron-deficient aryl chlorides and ammonia.


Notable Characteristics & Key Uses

• Chemical Structure: BippyPhos is a bipyrazole ligand featuring a di-tert-butylphosphine moiety that imparts high electron density, significant steric bulk, and strong sigma-donor character to the palladium center.
• Broad Solubility: BippyPhos exhibits excellent solubility in a wide range of common organic solvents, enabling its deployment across diverse reaction platforms and scales.
• Steric and Electronic Synergy: The pronounced steric shielding of BippyPhos accelerates the critical reductive elimination step in catalytic cycles, directly improving turnover frequency and product selectivity.
• Air Stability: BippyPhos is air-stable and straightforward to handle, making it well-suited for large-scale industrial applications.
• Versatility: Beyond C-N coupling, BippyPhos is equally effective for C-O and C-C bond-forming reactions, demonstrating broad applicability across coupling chemistries.
• Buchwald-Hartwig Amination (C-N Coupling): Particularly effective for coupling primary amines with aryl halides, including electron-deficient aryl chlorides. Widely used in the preparation of pharmaceutical intermediates and demonstrates exceptional efficiency for the monoarylation of ammonia and hydrazine.
• Suzuki-Miyaura and Heck Coupling: BippyPhos stabilizes active palladium complexes, markedly improving efficiency and selectivity in C-C bond-forming reactions.
• C-O Coupling: Functions as an efficient catalyst for coupling primary alcohols with (hetero)aryl halides.
• Hydroxylation: Employed in palladium-catalyzed hydroxylation of aryl halides to afford synthetically valuable phenols.
• Coordination Chemistry: Utilized in the investigation of metal-ligand interactions and the development of novel functional materials.

Recent Studies and Innovations 

1. Mechanochemical Synthesis: Mechanochemical methodologies have been applied to generate active Pd/BippyPhos catalysts in a solvent-free medium, successfully coupling aryl halides with amines in high yield. This approach underscores BippyPhos′s versatility beyond conventional solution-phase chemistry (Deniz et al., 2025).
2. Amination under Mild Conditions: Pd-BippyPhos complexes demonstrate remarkable efficacy in the amination of aryl fluorosulfates, affording biarylamines in excellent yields under mild conditions - surpassing alternative ligand systems tested under identical reaction parameters (Karthik S et al., 2024).

Legal Information

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SIGMA-ALDRICH is a registered trademark of Merck KGaA, Darmstadt, Germany

Sicherheitshinweise

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