901906

SPhos

95%, powder or crystals

• Synonim(y): 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos
• Wzór empiryczny (zapis Hilla): C₂₆H₃₅O₂P
• Numer CAS: 657408-07-6
• Masa cząsteczkowa: 410.53
• NACRES: NA.22
• UNSPSC Code: 12161600
• MDL number: MFCD05861611

Właściwości

• Nazwa produktu: SPhos, 95%
• assay: 95%
• form: powder or crystals
• 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: catalyst; reaction type: Cross Couplings, reagent type: ligand
• greener alternative product characteristics: Catalysis; Learn more about the Principles of Green Chemistry.
• sustainability: Sustainability features
• mp: 164-166 °C (lit.), 165.5 °C
• functional group: phosphine
• 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

Opis

General description

SPhos [2-Dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl] 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.

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Application

SPhos may be used as a ligand in the following processes:

• Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
• Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
• Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.

Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation

Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.

Legal Information

Usage subject to Patents: US 6307087; EP 1097158; JP 5758844; CA 2336691

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Informacja o środkach bezpieczeństwa

• Klasa składowania: 11 - Combustible Solids
• Co się dzieje?: WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable