901906

SPhos

95%

• Synonym(s): 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos
• Empirical Formula (Hill Notation): C₂₆H₃₅O₂P
• CAS Number: 657408-07-6
• Molecular Weight: 410.53
• MDL number: MFCD05861611
• UNSPSC Code: 12161600
• NACRES: NA.22

Properties

• 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
• 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

Description

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.

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable