638099

CyJohnPhos

97%

• Synonym(s): 2-(Dicyclohexylphosphino)biphenyl, (2-Biphenyl)dicyclohexylphosphine, Cyclohexyl JohnPhos
• Empirical Formula (Hill Notation): C₂₄H₃₁P
• CAS Number: 247940-06-3
• Molecular Weight: 350.48
• Beilstein/REAXYS Number: 8440533
• MDL number: MFCD01862441
• UNSPSC Code: 12352002
• PubChem Substance ID: 24882909
• NACRES: NA.22

Properties

• assay: 97%
• reaction suitability: reaction type: Cross Couplings; reagent type: ligand; reaction type: Arylations; reagent type: ligand; reaction type: Buchwald-Hartwig Cross Coupling Reaction; reagent type: ligand; reaction type: C-X Bond Formation; reagent type: ligand; reaction type: Hiyama Coupling; reagent type: ligand; reaction type: Methylations; reagent type: ligand; reaction type: Negishi Coupling; reagent type: ligand; reaction type: Oxidations; reagent type: ligand; reaction type: Suzuki-Miyaura Coupling
• mp: 102-106 °C (lit.)
• functional group: phosphine
• SMILES string: C1CCC(CC1)P(C2CCCCC2)c3ccccc3-c4ccccc4
• InChI: 1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2
• InChI key: LCSNDSFWVKMJCT-UHFFFAOYSA-N

Description

General description

CyJohnPhos [(2-Biphenyl)dicyclohexylphosphine] is an air-stable, bulky and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Learn more about Buchwald Phosphine Ligands

Application

CyJohnPhos may be used in combination with a nickel catalyst for the Suzuki-Miyaura arylation of tertiary benzylic acetates with aryl boroxines to produce diaryl and triaryl quaternary stereocenters.

Ligand employed in the palladium-catalysed synthesis of 1,3,5-tris(2′-aminophenyl)benzene, a core building block for potential ionic receptors.

Ligand for amination of aryl halides and triflates.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Safety Information

• hcodes: H413
• Hazard Classifications: Aquatic Chronic 4
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)