3-[3,5-bis(trifluoromethyl)phenyl]-1-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxynaphthalen-1-yl}naphthalen-2-ol

• ChemBase ID: 140831
• Molecular Formular: C36H18F12O2
• Molecular Mass: 710.5077584
• Monoisotopic Mass: 710.11151846
• SMILES: c1ccc2c(c1)cc(c(c2c1c2ccccc2cc(c1O)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)O)c1cc(cc(c1)C(F)(F)F)C(F)(F)F
• Canonical SMILES: Oc1c(cc2c(c1c1c(O)c(cc3c1cccc3)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)cccc2)c1cc(cc(c1)C(F)(F)F)C(F)(F)F
• InChI: InChI=1S/C36H18F12O2/c37-33(38,39)21-9-19(10-22(15-21)34(40,41)42)27-13-17-5-1-3-7-25(17)29(31(27)49)30-26-8-4-2-6-18(26)14-28(32(30)50)20-11-23(35(43,44)45)16-24(12-20)36(46,47)48/h1-16,49-50H
• InChIKey: PGXMYJSTCAQJBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[3,5-bis(trifluoromethyl)phenyl]-1-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxynaphthalen-1-yl}naphthalen-2-ol
• IUPAC Traditional name: 3-[3,5-bis(trifluoromethyl)phenyl]-1-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxynaphthalen-1-yl}naphthalen-2-ol
• Synonyms: (1S)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]1,1′-binaphthalene-2,2′-diol; (S)-(-)-3-3′-Bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol; (R)-(+)-3,3′-Bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol; (1S)-3,3′-双[3,5-双(三氟甲基)苯基]1,1′-联萘-2,2′-二醇; (S)-(-)-3-3′-双(3,5-双(三氟甲基)苯基)-1,1′-二-2-萘酚; (R)-(+)-3,3′-双(3,5-双(三氟甲基)苯基)-1,1′-二-2-萘酚

Database IDs

• CAS Number: 849939-13-5; 756491-54-0
• MDL Number: MFCD08689862
• PubChem SID: 162235069; 24885640; 24885224
• PubChem CID: 11664821

CALCULATED PROPERTIES

• Acid pKa: 8.629827
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 11.797819
• LogD (pH = 7.4): 11.773257
• Log P: 11.798139
• Molar Refractivity: 162.2236 cm^3
• Polarizability: 63.32134 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 215-219 °C; 216-220 °C
• Optical Rotation: [α]22/D 45°, c = 1 in chloroform; [α]22/D -56°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36; 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H319
• GHS Precautionary statements: P261-P305 + P351 + P338; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C36H18F12O2

DETAILS

Sigma Aldrich - 674591

Application
Precursor to a chiral Bronsted acid (680184) used to catalyze an enantioselective aza Diels-Alder reaction providing bicyclic lactams.1 Rare earth metal complexes of this chiral binapthol catalyze an intramolecular hydroamination of amino olefins leading to chiral pyrrolidines.2
Packaging
100 mg in glass bottle

Sigma Aldrich - 681539

Packaging
100 mg in glass bottle