13-(2-{13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-yl}phenyl)-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaene

• ChemBase ID: 135809
• Molecular Formular: C50H36P2
• Molecular Mass: 698.768362
• Monoisotopic Mass: 698.22922441
• SMILES: c1ccc2c(c1)ccc1c2c2c(ccc3c2cccc3)CP(C1)c1ccccc1P1Cc2ccc3ccccc3c2c2c(ccc3c2cccc3)C1
• Canonical SMILES: c1ccc(c(c1)P1Cc2ccc3c(c2c2c(C1)ccc1c2cccc1)cccc3)P1Cc2ccc3c(c2c2c(C1)ccc1c2cccc1)cccc3
• InChI: InChI=1S/C50H36P2/c1-5-15-41-33(11-1)21-25-37-29-51(30-38-26-22-34-12-2-6-16-42(34)48(38)47(37)41)45-19-9-10-20-46(45)52-31-39-27-23-35-13-3-7-17-43(35)49(39)50-40(32-52)28-24-36-14-4-8-18-44(36)50/h1-28H,29-32H2
• InChIKey: CQYMOICHLLQQAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-(2-{13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-yl}phenyl)-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaene
• IUPAC Traditional name: 13-(2-{13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-yl}phenyl)-13-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaene
• Synonyms: (R,R)-1,2-Bis[(R)-4,5-dihydro-3H-binaphtho(1,2-c:2′,1′-e)phosphepino]benzene; (R)-BINAPHANE; (R,R)-1,2-二[(R)-4,5-二氢-3H-联萘并(1,2-c:2′,1′-e)磷杂庚英并]苯; (R)-联萘

Database IDs

• CAS Number: 253311-88-5
• MDL Number: MFCD06658114
• PubChem SID: 162230080; 24883783
• PubChem CID: 9896414

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 12.573961
• LogD (pH = 7.4): 12.6882925
• Log P: 12.6906
• Molar Refractivity: 220.0914 cm^3
• Polarizability: 93.71492 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >200 °C (dec.)

Safety Information

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

Product Information

• Empirical Formula (Hill Notation): C50H36P2

DETAILS

Sigma Aldrich - 650854

Application
(R)-Binaphane shows excellent enantioselectivity (up to >99% ee) for hydrogenation of E/Z-isomeric mixtures of β-substituted arylenamides.6
Chiral Quest Phosphine Ligands for Asymmetric HydrogenationCatalyst involved in:
• Enantioselective anilinosulfonamide allyl alcohol cyclization1
• Synthesis of β-trifluoromethyl α-amino acids2
• Phosphine-catalyzed cycloadditions of aldehydes and ketoketenes3
• Dimerization of ketoketenes4
• Enantioselective carbonyl-ene reactions via palladium and platinum derivatives5