bis(rhodiumol); bis({1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane)

• ChemBase ID: 140425
• Molecular Formular: C88H66O2P4Rh2
• Molecular Mass: 1485.170484
• Monoisotopic Mass: 1484.21233587
• SMILES: c1ccc(cc1)P(c1ccccc1)c1ccc2ccccc2c1c1c2ccccc2ccc1P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccc2ccccc2c1c1c2ccccc2ccc1P(c1ccccc1)c1ccccc1.O[Rh].O[Rh]
• Canonical SMILES: c1ccc(cc1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1ccccc1)c1ccccc1)cccc2)c1ccccc1.c1ccc(cc1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1ccccc1)c1ccccc1)cccc2)c1ccccc1.O[Rh].O[Rh]
• InChI: InChI=1S/2C44H32P2.2H2O.2Rh/c2*1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38;;;;/h2*1-32H;2*1H2;;/q;;;;2*+1/p-2
• InChIKey: PWIUOLBVYNHREE-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(rhodiumol); bis({1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane)
• IUPAC Traditional name: bis(binap); bis(rhodiumol)
• Synonyms: Hydroxy[-(S)-BINAP]-rhodium(I) Dimer; 羟基[-(S)-BINAP]-铑(I) 二聚体

Database IDs

• MDL Number: MFCD08561132
• PubChem SID: 162234669; 24884495
• PubChem CID: 11982518

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 11.8554
• LogD (pH = 7.4): 11.8554
• Log P: 11.8554
• Molar Refractivity: 195.2244 cm^3
• Polarizability: 80.66715 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3

Product Information

• Purity: 90%
• Impurities: 3-5% ethanol; 3-5% THF
• Empirical Formula (Hill Notation): C88H66O2P4Rh2

DETAILS

Sigma Aldrich - 661007

Application
Catalyst employed in an asymmetric 1,6-addition of arylzinc reagents to dienones leading to chiral 5-substituted enones.1 Also used in an asymmetric 1,4-addition of organoboron reagents to cyclic and acyclic α,β-unsaturated ketones with excellent enantioselectivity.2
Efficient and Selective Catalysts for Asymmetric Synthesis
Packaging
1 g in glass bottle
250 mg in glass bottle