3-(4-hydroxy-2-phenylphenanthren-3-yl)-2-phenylphenanthren-4-ol

• ChemBase ID: 140151
• Molecular Formular: C40H26O2
• Molecular Mass: 538.63324
• Monoisotopic Mass: 538.19328007
• SMILES: c1ccc(cc1)c1cc2ccc3ccccc3c2c(c1c1c(cc2ccc3ccccc3c2c1O)c1ccccc1)O
• Canonical SMILES: Oc1c(c(cc2c1c1ccccc1cc2)c1ccccc1)c1c(cc2c(c1O)c1ccccc1cc2)c1ccccc1
• InChI: InChI=1S/C40H26O2/c41-39-35-29(21-19-27-15-7-9-17-31(27)35)23-33(25-11-3-1-4-12-25)37(39)38-34(26-13-5-2-6-14-26)24-30-22-20-28-16-8-10-18-32(28)36(30)40(38)42/h1-24,41-42H
• InChIKey: UFYXKDMLGBKHIC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxy-2-phenylphenanthren-3-yl)-2-phenylphenanthren-4-ol
• IUPAC Traditional name: 3-(4-hydroxy-2-phenylphenanthren-3-yl)-2-phenylphenanthren-4-ol
• Synonyms: (S)-2,2′-Diphenyl-(4-biphenanthrol); (S)-VAPOL; (R)-2,2′-Diphenyl-3,3′-(4-biphenanthrol); (R)-VAPOL; (S)-2,2′-二苯基-(4-联菲酚); (R)-2,2′-二苯基-3,3′-(4-联菲酚)

Database IDs

• CAS Number: 147702-16-7; 147702-15-6
• EC Number: 200-838-9
• MDL Number: MFCD11617354
• PubChem SID: 24885269; 162234395; 24885273
• PubChem CID: 10918556

CALCULATED PROPERTIES

• Acid pKa: 8.467874
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 10.265234
• LogD (pH = 7.4): 10.229908
• Log P: 10.265698
• Molar Refractivity: 171.2292 cm^3
• Polarizability: 75.49718 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 185-191 °C; 225-229 °C
• Optical Rotation: [α]20/D 128°, c = 1 in chloroform; [α]20/D -144°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 37/38-40-41; 40
• Safety Statements: 23-24/25-36/37; 26-36/37/39
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H315-H318-H335-H351; H351
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P281

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C40H26O2

DETAILS

Sigma Aldrich - 675334

Application
VAPOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.1,2,3
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 675210

Application
VAPOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.1,2,3
Packaging
100, 500 mg in glass bottle