638021

DavePhos

97%

• Synonym(s): 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl
• Empirical Formula (Hill Notation): C₂₆H₃₆NP
• CAS Number: 213697-53-1
• Molecular Weight: 393.54
• MDL number: MFCD02183572
• UNSPSC Code: 12352116
• PubChem Substance ID: 24882905
• NACRES: NA.22

Properties

• Quality Level: 200
• 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: Hydroaminations; reagent type: ligand; reaction type: Kumada Coupling; reagent type: ligand; reaction type: Negishi Coupling; reagent type: ligand; reaction type: Suzuki-Miyaura Coupling
• mp: 121-124 °C (lit.)
• functional group: phosphine
• SMILES string: CN(C)c1ccccc1-c2ccccc2P(C3CCCCC3)C4CCCCC4
• InChI: 1S/C26H36NP/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22/h9-12,17-22H,3-8,13-16H2,1-2H3
• InChI key: ZEMZPXWZVTUONV-UHFFFAOYSA-N

Description

Application

DavePhos may be used as a ligand in the following reactions:

• Palladium catalyzed sp³ arylation of 2-substituted-N-iminopyridinium ylides with different aryl chlorides to yield functionalized pyridines.
• Preparation of functionalized benzylic sulfones via palladium-catalyzed Negishi cross-coupling between alkyl sulfones and aryl halides.
• C-C Coupling of 3-haloquinolines with aryl sulfinates via palladium-catalyzed desulfitative arylation to form the corresponding biaryl compounds.

Ligand used in a Pd-catalyzed Suzuki aryl-aryl coupling leading to benzodioxepines.

Learn more about Buchwald Phosphine Ligands

Useful ligand for Pd-catalyzed C-N bond formation; amination of aryl halides containing hydroxyl, amide, or enolizable ketones.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves