PMC2008

AdBrettPhos

≥98%, ISOM8^™

• Synonim(y): AdBrettPhos, 2-(Di-1-adamantylphosphino)-3,6-diMethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl, Di-Ad-BrettPhos
• Wzór empiryczny (zapis Hilla): C₄₃H₆₁O₂P
• Numer CAS: 1160861-59-5
• Masa cząsteczkowa: 640.92
• MDL number: MFCD23379935
• UNSPSC Code: 12352128
• PubChem Substance ID: 329767360
• NACRES: NA.22
• eCl@ss: 32151101

Właściwości

• product line: ISOM8^™
• Quality Segment: 300
• assay: (HPLC), ≥98%
• form: solid
• mol wt: 640.92
• reaction suitability: reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: ligand
• mp: 231-235 °C
• application(s): diagnostic assay manufacturing
• functional group: phosphine
• storage temp.: room temp
• SMILES string: COc1ccc(OC)c(c1P(C23CC4CC(CC(C4)C2)C3)C56CC7CC(CC(C7)C5)C6)-c8c(cc(cc8C(C)C)C(C)C)C(C)C
• InChI: 1S/C43H61O2P/c1-25(2)34-17-35(26(3)4)39(36(18-34)27(5)6)40-37(44-7)9-10-38(45-8)41(40)46(42-19-28-11-29(20-42)13-30(12-28)21-42)43-22-31-14-32(23-43)16-33(15-31)24-43/h9-10,17-18,25-33H,11-16,19-24H2,1-8H3
• InChI key: NMGHOZQCYNKWBG-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.

Application

Recent Studies and Innovations:  

1. Selective Primary Amination of Hindered Arenes: A catalyst system incorporating beta-methylnaphthyl (MeNAP) palladium bromide with AdBrettPhos successfully resolved the competition between single and double arylation, achieving selective introduction of a primary amino group into sterically congested aromatic substrates (Xue et al., 2023).
2. Amidation of Five-Membered Heterocyclic Bromides: Five-membered heterocycles present significant challenges in palladium-catalyzed amidation due to their electron-rich nature and the propensity of heteroatoms to coordinate and deactivate the catalyst. The use of [{(allyl)PdCl}₂] in combination with AdBrettPhos markedly improves catalytic efficiency for these demanding substrates (Su et al., 2012).
3. Thermally and Air-Stable Precatalysts: Precatalysts derived from PdCl2, Pd(OAc)₂, or [(cinnamyl)PdCl]₂ in combination with AdBrettPhos exhibit excellent thermal stability at room temperature and notable air/moisture stability, making them ideal for cross-coupling reactions without the need for additional base required by more conventional systems (Lee et al., 2014)

• Buchwald Phosphine Ligands for chemical Synthesis 
• Common applications 

AdBrettPhos is a bulky biarylphosphine ligand developed by the Buchwald group, distinguished by its sterically demanding adamantyl substituents. It enables highly efficient palladium-catalyzed cross-coupling reactions and is particularly noted for forming C-N, C-O, C-F, C-CF₃, and C-S bonds under conditions that challenge conventional ligand systems.

Notable Characteristics & Key Uses

• Sterically Demanding Structure: The bulky adamantyl groups create a highly hindered coordination environment, enabling selective bond formations that are otherwise inaccessible with less congested ligands.
• Exceptional Stability: AdBrettPhos is frequently deployed as part of air-, moisture-, and thermally stable palladium G3 (3rd Generation) and G6 (6th Generation) precatalysts, simplifying handling while maintaining consistently high catalytic activity.
• Broad Bond-Forming Capability: Forms a diverse array of bond types - C-C, C-N, C-O, C-F, C-CF3, and C-S - including reactions previously considered difficult or impossible with conventional ligands.
• Selectivity for Monoarylation: Renowned for its ability to promote selective monoarylation of ammonia and coupling of weak nucleophiles, while effectively suppressing undesirable diarylation side products.
• User-Friendly Precatalyst Systems: Compatible precatalyst systems allow for low catalyst loadings, abbreviated reaction times, and simplified preparation and handling protocols suitable for research and industrial scales.
• Suzuki-Miyaura Cross-Coupling (C-C): Enables efficient biaryl and aryl-alkyl coupling across a broad substrate scope, including challenging aryl chlorides.
• Buchwald-Hartwig Amination (C-N): Particularly powerful for the amidation of challenging five-membered heterocyclic halides and the selective monoarylation of ammonia.
• Heck, Hiyama, Negishi, Sonogashira, and Stille Couplings: Versatile across multiple palladium-catalyzed C-C bond-forming reactions.
• C-O Cross-Coupling: Facilitates coupling of primary alcohols with aryl electrophiles to form ethers and related products.
• Fluorination and Trifluoromethylation: Enables trifluoromethylation of aryl chlorides and synthesis of aryl fluorides, including highly challenging transformations.
  

Legal Information

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

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

Disclaimer

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Informacja o środkach bezpieczeństwa

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