PMC2001

tBuBrettPhos

≥98%, ISOM8^™

• Synonym(e): t-BuBrett Phos, t-BuBrettPhos, [3,6-Dimethoxy-2′,4′,6′-tris-(1-methylethyl)-[1,1′-biphenyl]-2-yl]-bis-(1,1-dimethylethyl)-phosphin, tert-ButylBrettPhos
• Empirische Formel (Hill-System): C₃₁H₄₉O₂P
• CAS-Nummer: 1160861-53-9
• Molekulargewicht: 484.69
• UNSPSC Code: 12352128
• NACRES: NA.22
• PubChem Substance ID: 329764610
• MDL number: MFCD13181930

Eigenschaften

• product line: ISOM8^™
• Quality Segment: 300
• assay: (HPLC), ≥98%
• form: solid
• mol wt: 484.69
• reaction suitability: reaction type: Arylations, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: C-X Bond Formation, reaction type: Cross Couplings, reaction type: Fluorinations
• mp: 170-171 °C (Lit.), 166-170 °C
• application(s): diagnostic assay manufacturing; diagnostic assay manufacturing; life science and biopharma
• functional group: phosphine
• storage temp.: room temp
• SMILES string: COc1ccc(OC)c(c1P(C(C)(C)C)C(C)(C)C)-c2c(cc(cc2C(C)C)C(C)C)C(C)C
• InChI: 1S/C31H49O2P/c1-19(2)22-17-23(20(3)4)27(24(18-22)21(5)6)28-25(32-13)15-16-26(33-14)29(28)34(30(7,8)9)31(10,11)12/h15-21H,1-14H3
• InChI key: REWLCYPYZCHYSS-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 dossiers and other quality documentation for this product, provided with support of our Elevate Program.

Application

• Buchwald Phosphine Ligands forchemical Synthesis
• Common applications

tBuBrettPhosis a phosphine ligand developed by the Buchwald group that enables highly efficient palladium-catalyzed cross-coupling reactions. This ligand is essential for synthesizing complex organic molecules in pharmaceutical and materials science applications.
Notable characteristics & key uses:

• Selectivity: The bulky tert-butyl groups provide exceptional steric control, preventing unwanted side reactions and enhancing selectivity.
• Electronic Properties: Strong electron-donating ability due to alkyl substituents and methoxy groups, stabilizing low-valent metal intermediates.
• Air Stability: Unlike traditional phosphine ligands, tBuBrettPhos demonstrates remarkable resistance to air, moisture, and thermal degradation
• Catalytic Applications: tBuBrettPhos is widely used in various reactions, including cross-coupling reactions, such as Suzuki and Sonogashira reactions, due to its ability tostabilize metal-ligand complexes.
• Cross-Coupling Reactions: tBuBrettPhos enables efficient Suzuki-Miyaura, Buchwald-Hartwig, Heck, and Sonogashira coupling reactions under mild conditions with exceptional selectivity and functional group tolerance, facilitating the formation of carbon-carbon bonds
• Phosphine-Catalyzed Reactions: tBuBrettPhos can act as a catalyst or ligand in various phosphine-catalyzed transformations, enhancing reaction rates and selectivity
• C-H Activation: It has been employed in C-H activation processes, allowing for the functionalization of hydrocarbons under mild conditions.
• Asymmetric Synthesis: tBuBrettPhos is used in asymmetric synthesis to produce chiral molecules, often in conjunction with transition metal catalysts to achieve enantioselectivity.
• Organometallic Chemistry: It plays a role in the stabilization of organometallic complexes, which can be crucial for the development of new catalytic systems.

Recent Studies and Innovations:Selective Monoarylation Catalysis: Pd-methylnaphthyl(MeNAP)-tBuBrettPhos complexes demonstrate exceptional selectivity as pre-catalysts for the monoarylation of ammonia and hydrazine, with theirsterically hindered nature preventing over-arylation and enabling precise control over product formation. (Bingxiang Xue et al., 2024

C-O Cross-Coupling with Fluorinated Alcohols: A highly effective protocol has been developed forcross-coupling (hetero)aryl bromides with fluorinated alcohols using tBuBrettPhos Pd G3 and Cs₂CO₃ in toluene, offering short reaction times, excellent functional group tolerance, and broad compatibility with both electron-rich and electron-poor (hetero)arenes. (Robert Szpera et al., 2020)

Nitroaromatic Synthesis: Under weakly basic conditions, tBuBrettPhos supported palladium catalysis enables the efficient transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics, displaying broad substrate scope and excellent functional group compatibility. (Brett P. et al., 2009)

Buchwald-Phosphin-Liganden für die chemische Synthese

Legal Information

ISOM8 is a trademark of Sigma-Aldrich Co. LLC

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

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

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable