Skip to Content
Merck
CN
All Photos(3)

Key Documents

View All Documentation

638021

Sigma-Aldrich

DavePhos

97%

Synonym(s):

2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

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

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

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.

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBP0503
SHBN5080
0000003497
SHBH1275V
14597DJV

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Biaryl axis as a stereochemical relay for the enantioselective synthesis of antimicrotubule agents.
Agnès Joncour et al.
Angewandte Chemie (International ed. in English), 45(25), 4149-4152 (2006-05-12)
Palladium-catalyzed desulfitative arylation of 3-haloquinolines with arylsulfinates.
Colomb J and Billard T.
Tetrahedron Letters, 54(11), 1471-1474 (2013)
Palladium-catalyzed benzylic CH insertion of 2-substituted N-iminopyridinium ylides.
Mousseau JJ, et al.
Organic Letters, 10(8), 1641-1643 (2008)
Palladium-catalyzed Negishi a-arylation of alkylsulfones.
Zhou G, et al.
Tetrahedron Letters, 51(6), 939-941 (2010)
George R Kracke et al.
ChemMedChem, 10(1), 62-67 (2014-11-26)
Clinically there is a need for local anesthetics with a greater specificity of action on target cells and longer duration. We have synthesized a series of local anesthetic derivatives we call boronicaines in which the aromatic phenyl ring of lidocaine
View All Related Papers

Articles

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Related Content

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service