2-[2-(dicyclohexylphosphanyl)phenyl]-N,N-dimethylaniline

• ChemBase ID: 10387
• Molecular Formular: C26H36NP
• Molecular Mass: 393.544501
• Monoisotopic Mass: 393.25853679
• SMILES: c1(c2c(cccc2)N(C)C)c(cccc1)P(C1CCCCC1)C1CCCCC1
• Canonical SMILES: CN(c1ccccc1c1ccccc1P(C1CCCCC1)C1CCCCC1)C
• InChI: 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
• InChIKey: ZEMZPXWZVTUONV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(dicyclohexylphosphanyl)phenyl]-N,N-dimethylaniline
• IUPAC Traditional name: 2-[2-(dicyclohexylphosphanyl)phenyl]-N,N-dimethylaniline
• Synonyms: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl; 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl; DavePhos; 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl; 2-二环己膦基-2′-(N,N-二甲胺)联苯

Database IDs

• CAS Number: 213697-53-1
• MDL Number: MFCD02183572
• PubChem SID: 24882905; 160973694
• PubChem CID: 2734217

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.4006815
• LogD (pH = 7.4): 6.784601
• Log P: 7.0772
• Molar Refractivity: 123.5625 cm^3
• Polarizability: 49.604805 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 115-119°C; 121-124 °C(lit.)
• Ligand For: Arylations; Buchwald-Hartwig Cross Coupling Reaction; Hydroaminations; Kumada Coupling; Negishi Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: AIR SENSITIVE
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C26H36NP

DETAILS

Sigma Aldrich - 638021

Application
Ligand used in a Pd-catalyzed Suzuki aryl-aryl coupling leading to benzodioxepines.1
Useful ligand for Pd-catalyzed C-N bond formation; amination of aryl halides containing hydroxyl, amide, or enolizable ketones.
Packaging
1, 5, 25, 100 g in glass bottle
Legal Information
Usage subject to US Patents 6307087 and 6395916.