{2-[2-(diphenylphosphanyl)-6-methoxyphenyl]-3-methoxyphenyl}diphenylphosphane

• ChemBase ID: 141348
• Molecular Formular: C38H32O2P2
• Molecular Mass: 582.607002
• Monoisotopic Mass: 582.18775352
• SMILES: COc1cccc(c1c1c(cccc1P(c1ccccc1)c1ccccc1)OC)P(c1ccccc1)c1ccccc1
• Canonical SMILES: COc1cccc(c1c1c(OC)cccc1P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C38H32O2P2/c1-39-33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)38-34(40-2)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3
• InChIKey: KRJVQCZJJSUHHO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[2-(diphenylphosphanyl)-6-methoxyphenyl]-3-methoxyphenyl}diphenylphosphane
• IUPAC Traditional name: {2-[2-(diphenylphosphanyl)-6-methoxyphenyl]-3-methoxyphenyl}diphenylphosphane
• Synonyms: (R)-(+)-MeO-BIPHEP; SL-A101-1; (R)-(+)-2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; (R)-(+)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine); (S)-(-)-MeO-BIPHEP; SL-A101-2; (S)-(-)-2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; (S)-(-)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine); (R)-(+)-2,2′-双(二苯基膦)-6,6′-二甲氧-1,1′-联苯; (R)-(+)-(6,6′-二甲氧联苯-2,2′-二基)双(二苯基膦); (S)-(-)-2,2′-双(二苯基膦)-6,6′-二甲氧-1,1′-联苯; (S)-(-)-(6,6′-二甲氧联苯-2,2′-二基)双(二苯基膦)

Database IDs

• CAS Number: 133545-17-2; 133545-16-1
• MDL Number: MFCD03095430
• Beilstein Number: 4790083
• PubChem SID: 162235582; 24857757; 24857759
• PubChem CID: 4246603

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 9.3456
• LogD (pH = 7.4): 9.3456
• Log P: 9.3456
• Molar Refractivity: 175.2504 cm^3
• Polarizability: 70.29479 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 8
• 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: ≥97%
• Optical Purity: ee: ≥99%
• Empirical Formula (Hill Notation): C38H32O2P2

DETAILS

Sigma Aldrich - 29510

Application
Atropisomeric diphosphine; the Rh(I) complex is employed for highly enantioselective asymmetric isomerization of allylamines to enamines4,5; the Ru(II) complex hydrogenates β-keto esters in high enantioselectivity6,7; the Pd(0) complex for cyclization of hydroxy allylic carbonates8.
Atropisomeric MeOBIPHEP ligands
• Hydrogenation of α- and β-functionalized ketones1
• Hydrogenation of heteroarenes2
• C-C coupling reactions3
General description
sold in collaboration with Solvias AG
Packaging
1, 5 g in glass bottle
100, 500 mg in glass bottle

Sigma Aldrich - 29511

General description
sold in collaboration with Solvias AG
Packaging
1, 5 g in glass bottle
100, 500 mg in glass bottle
Application
Atropisomeric MeOBIPHEP ligands
• C-C coupling reactions1
• Ligand for palladium-catalyzed intramolecular allylic alkylation of unsaturated amides2
• Enantioselective hydrogenation of a-amino-β-keto ester hydrochlorides catalyzed by an iridium complex3
• Asymmetric hydrogenation of aromatic ketones4