PMC2007

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

≥98%, ISOM8^™

• Synonym(e): S-Phos, SPhos
• Empirische Formel (Hill-System): C₂₆H₃₅O₂P
• CAS-Nummer: 657408-07-6
• Molekulargewicht: 410.53
• UNSPSC Code: 12352128
• NACRES: NA.22
• MDL number: MFCD05861611

Eigenschaften

• Quality Segment: 300
• product line: ISOM8^™
• assay: (HPLC), ≥98%
• form: solid
• mol wt: 410.53
• reaction suitability: reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, 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: catalyst, reagent type: ligand
• greener alternative product score: old score: 10; new score: 1; Find out more about DOZN™ Scoring
• greener alternative product characteristics: Waste Prevention; Less Hazardous Chemical Syntheses; Inherently Safer Chemistry for Accident Prevention; Learn more about the Principles of Green Chemistry.
• sustainability: Sustainability features
• mp: 164-166 °C °C (Lit.), 164-166 °C (lit.)
• application(s): diagnostic assay manufacturing
• functional group: phosphine
• storage temp.: 15-25°C
• SMILES string: COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4
• InChI: 1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3
• InChI key: VNFWTIYUKDMAOP-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. 

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 “Waste Prevention”, “Atom Economy” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

Application

Universell genutzter Ligand für die Suzuki-Miyaura-Kupplung; Arylchloride, gehinderte Biaryle, Heterobiaryle.

• Buchwald Phosphine Ligands for chemical Synthesis 
• Common applications

SPhos, is a highly active, air-stable biarylphosphine ligand developed by the Buchwald group. It is distinguished by its potent electron-donating methoxy substituents and bulky dicyclohexylphosphine moiety, making it one of the most versatile and widely adopted ligands in palladium-catalyzed cross-coupling chemistry.

• Electron-Rich Design: The methoxy groups at the 2′ and 6′ positions of the biphenyl backbone render SPhos strongly electron-rich, elevating electron density at the palladium center and facilitating oxidative addition - often the rate-determining step in cross-coupling catalysis
• Sterically Bulky: The dicyclohexylphosphine moiety and ortho-substituents on the biphenyl framework provide substantial steric shielding around the metal center, suppressing undesirable side reactions

• Air Stability & High Thermal Stability: SPhos is air-stable as a solid, simplifying storage and handling without the need for inert atmosphere techniques and SPhos-based catalysts withstand elevated reaction temperatures.
• Suzuki-Miyaura Cross-Coupling: Flagship application of SPhos; effective for unactivated aryl chlorides, sterically hindered biaryls, heteroaryl systems, and macrocyclic natural product synthesis, often under mild or room-temperature conditions.
• Buchwald-Hartwig Amination: Highly active for C–N bond formation, including coupling of aryl chlorides with primary amines.
• Other Cross-Coupling Reactions: Applied in Heck, Negishi, Hiyama, Stille, Sonogashira, and borylation reactions of aryl halides.
• Pharmaceutical and Natural Product Synthesis: SPhos enables the synthesis of bioactive molecules such as biaryl amino acids found in the chloropeptin family of antibiotics, owing to its capacity to facilitate complex bond formations while suppressing side reactions including racemization.
• Industrial Applications: The air stability and operational simplicity of SPhos-based catalysts render them suitable for large-scale production of fine chemicals and advanced material.

Recent Studies and Innovations:

1. Aqueous-Phase Borylation with Stable Precatalysts: SPhos plays a critical role in enhancing the efficiency and yield of palladium-catalyzed [Pd(OAc)2] borylation reactions conducted under aqueous conditions. Its ability to stabilize active palladium species and facilitate reactions with diverse substrates makes it invaluable in the synthesis of active pharmaceutical ingredients (Compagno et al., 2024).
2. Ligand medication reaction: Replacing the -PCy2 group in SPhos with diphenylphosphine (-PPh2) in combination with Pd(OAc)2 affords a catalyst system that surpasses conventional SPhos in the arylation of polyfluoroarenes under mild reaction conditions (Yuen et al., 2018).
3. Suzuki-Miyaura & Heck reactions: SPhos-based systems in combination with palladium(II) salts such as Pd(OAc)2 provide effective precatalysts for Suzuki-Miyaura and Heck reactions. Optimization of the pre-catalyst reduction process to generate active Pd(0) species is key to achieving optimal performance (Fantoni et al., 2025).

Legal Information

Verwendung unterliegt Patenten: US 6307087; 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

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

Sicherheitshinweise

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