benzylbis(3R,5S,7s)-adamantan-1-ylphosphane

• ChemBase ID: 141306
• Molecular Formular: C27H37P
• Molecular Mass: 392.556441
• Monoisotopic Mass: 392.26328781
• SMILES: c1ccc(cc1)CP([C@@]12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3)[C@@]12C[C@H]3C[C@@H](C1)C[C@H](C2)C3
• Canonical SMILES: C1[C@@H]2C[C@@H]3C[C@@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)Cc1ccccc1
• InChI: InChI=1S/C27H37P/c1-2-4-19(5-3-1)18-28(26-12-20-6-21(13-26)8-22(7-20)14-26)27-15-23-9-24(16-27)11-25(10-23)17-27/h1-5,20-25H,6-18H2/t20-,21+,22-,23-,24+,25-,26-,27-
• InChIKey: ANIAFEJRWQDKDV-ANIFQACUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzylbis(3R,5S,7s)-adamantan-1-ylphosphane
• IUPAC Traditional name: benzylbis(3R,5S,7s)-adamantan-1-ylphosphane
• Synonyms: cataCXium® ABn; Di(1-adamantyl)benzylphosphine; 苄基二金刚烷基膦

Database IDs

• CAS Number: 395116-70-8
• MDL Number: MFCD05861603
• Beilstein Number: 9359745
• PubChem SID: 162235540
• PubChem CID: 11271420

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.3375263
• LogD (pH = 7.4): 5.337606
• Log P: 5.5221
• Molar Refractivity: 122.848 cm^3
• Polarizability: 47.40076 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C27H37P

DETAILS

Sigma Aldrich - 671800

General description
sold in collaboration with Solvias AG
Packaging
1, 5 g in glass bottle
Legal Information
US7148176
cataCXium is a registered trademark of Evonik Degussa GmbH
Application
Catalyst for:
• Sonogashira coupling reaction1
• Ruthenium-catalyzed amination of secondary alcohols. with ammonia2
• Rhodium-catalyzed regioselective hydroformylation of alkenes3
• Reductive carbonylation4
• Suzuki coupling reaction5
Protocols & Applications
Efficient Suzuki Coupling with cataCXium Ligands and Complexes