dicyclohexyl[2-(2-methyl-1,3-dioxolan-2-yl)phenyl]phosphane

• ChemBase ID: 140542
• Molecular Formular: C22H33O2P
• Molecular Mass: 360.469981
• Monoisotopic Mass: 360.22181693
• SMILES: CC1(OCCO1)c1ccccc1P(C1CCCCC1)C1CCCCC1
• Canonical SMILES: CC1(OCCO1)c1ccccc1P(C1CCCCC1)C1CCCCC1
• InChI: InChI=1S/C22H33O2P/c1-22(23-16-17-24-22)20-14-8-9-15-21(20)25(18-10-4-2-5-11-18)19-12-6-3-7-13-19/h8-9,14-15,18-19H,2-7,10-13,16-17H2,1H3
• InChIKey: ZQASITYRQOCACA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dicyclohexyl[2-(2-methyl-1,3-dioxolan-2-yl)phenyl]phosphane
• IUPAC Traditional name: dicyclohexyl[2-(2-methyl-1,3-dioxolan-2-yl)phenyl]phosphane
• Synonyms: 2′-(Dicyclohexylphosphino)acetophenone ethylene ketal; 2′-(二环己基膦)苯乙酮缩乙二醇

Database IDs

• CAS Number: 221187-50-4
• MDL Number: MFCD08705257
• PubChem SID: 24885298; 162234786
• PubChem CID: 11078910

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.189409
• LogD (pH = 7.4): 5.479258
• Log P: 5.4876
• Molar Refractivity: 104.3987 cm^3
• Polarizability: 41.709194 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 85-92 °C

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C22H33O2P

DETAILS

Sigma Aldrich - 675709

Application
A P-O ligand that in combination with Pd2(dba)3 (cat. no. 328774) provides an active catalyst that effectively cross-couples a variety of arylboronic acids with aryl chlorides containing either electron-rich or electron-poor substituents.2
Cocatalyst for:
• Palladium-catalyzed amination reactions1
• Palladium/P,O-Ligand-catalyzed Suzuki cross-coupling2
Packaging
1, 5 g in glass bottle
Protocols & Applications
Efficient Suzuki Coupling with Symphos Ligands