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Merck

638021

Sigma-Aldrich

DavePhos

97%

Synonym(s):

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

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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

Key Documents

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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

Related Categories

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP0503
SHBN5080
SHBH1275V
14597DJV
14597DJ

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Palladium-catalyzed desulfitative arylation of 3-haloquinolines with arylsulfinates.
Colomb J and Billard T.
Tetrahedron Letters, 54(11), 1471-1474 (2013)
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 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

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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.

Catalexis 촉매 스크리닝 플랫폼

Catalexis 플랫폼은 촉매 선택을 디지털 방식으로 최적화하여 교차 결합 반응에 가장 효과적인 포스핀 리간드를 식별함으로써 촉매 작용을 향상합니다.

Phosphine Ligand Application Guide

Phosphine Ligand Application Guide

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