675156

(R)-VANOL

97%

• Synonym(s): (R)-3,3′-Diphenyl-2,2′-bi-1-naphthalol, (R)-3,3′-Diphenyl-2,2′-bi-1-naphthol
• Empirical Formula (Hill Notation): C₃₂H₂₂O₂
• CAS Number: 147702-13-4
• Molecular Weight: 438.52
• MDL number: MFCD08459338
• UNSPSC Code: 12352005
• PubChem Substance ID: 24885264
• NACRES: NA.22

Properties

• assay: 97%
• form: solid
• optical activity: [α]20/D +310°, c = 1 in chloroform
• mp: 200-204 °C
• functional group: phenyl
• SMILES string: Oc1c(c(cc2ccccc12)-c3ccccc3)-c4c(O)c5ccccc5cc4-c6ccccc6
• InChI: 1S/C32H22O2/c33-31-25-17-9-7-15-23(25)19-27(21-11-3-1-4-12-21)29(31)30-28(22-13-5-2-6-14-22)20-24-16-8-10-18-26(24)32(30)34/h1-20,33-34H
• InChI key: NDTDVKKGYBULHF-UHFFFAOYSA-N

Description

Application

(R)-VANOL is a vaulted biaryl ligand that may be used in the following processes:

• Transformation of 3-substituted cyclobutanones to enantiopure γ-butyrolactones via asymmetric Baeyer-Villiger Reaction in the presence of an aluminum catalyst.
• Asymmetric aziridination of N-(4-(Methylsulfonyl)benzylidene)diphenylmethanamine to form (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl) aziridine-2-carboxylate.
• Conjugate addition of terminal alkynes to 2-arylidene-1,3-diketones with high enantioselectivity in the presence of diethyl zinc.

VANOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H315,H318,H335,H413
• pcodes: P273 - P280 - P302 + P352 - P305 + P351 + P338 + P310
• Hazard Classifications: Aquatic Chronic 4 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves