(S)-Vanol

Base Information

• Chemical Name: (S)-Vanol
• CAS No.: 147702-13-4
• Molecular Formula: C₃₂H₂₂O₂
• Molecular Weight: 438.525
• European Community (EC) Number: 633-946-3,633-947-9
• Nikkaji Number: J2.959.661A,J737.938B,J2.469.583B
• Mol file: 147702-13-4.mol

Synonyms:(S)-VANOL;147702-13-4;147702-14-5;(R)-VANOL;(2R)-3,3'-Diphenyl[2,2'-binaphthalene]-1,1'-diol;(2S)-3,3'-Diphenyl[2,2'-binaphthalene]-1,1'-diol;2-(1-hydroxy-3-phenylnaphthalen-2-yl)-3-phenylnaphthalen-1-ol;(2S)-(-)-3,3'-Diphenyl-[2,2'-binaphthalene]-1,1'-diol;[2,2'-Binaphthalene]-1,1'-diol, 3,3'-diphenyl-, (2R)-;MFCD08459338;vanol;SCHEMBL6130223;(R)-VANOL, 97%;(S)-VANOL, 97%;BS-53294;SY073054;SY073055;CS-0085175;CS-0086058;FT-0734105;FT-0766549;E76901;E76902;J-008395;J-008396;(2R)-(+)-3,3'-Diphenyl-[2,2'-binaphthalene]-1,1'-diol;[2,2'-Binaphthalene]-1,1'-diol, 3,3'-diphenyl-, (2S)-;(2R)-3,3 inverted exclamation mark -Diphenyl[2,2 inverted exclamation mark -binaphthalene]-1,1 inverted exclamation mark -diol;(2S)-3,3 inverted exclamation mark -Diphenyl[2,2 inverted exclamation mark -binaphthalene]-1,1 inverted exclamation mark -diol

Chemical Property of (S)-Vanol

Chemical Property:

• Vapor Pressure: 4.69E-14mmHg at 25°C
• Melting Point: 200-204 °C
• Refractive Index: 1.727
• Boiling Point: 580.1°C at 760 mmHg
• PKA: 7.71±0.50(Predicted)
• Flash Point: 251.8°C
• PSA: 40.46000
• Density: 1.251g/cm³
• LogP: 8.40520
• Storage Temp.: 2-8°C
• XLogP3: 8.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 438.161979940
• Heavy Atom Count: 34
• Complexity: 593

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2R)-(+)-3,3'-Diphenyl-[2,2'-binaphthalene]-1,1'-diol, min. 98% (R)-VANOL ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=CC=CC=C3C(=C2C4=C(C5=CC=CC=C5C=C4C6=CC=CC=C6)O)O
• Uses: VANOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

Technology Process of (S)-Vanol

There total 5 articles about (S)-Vanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.2%

3-phenylnaphthalen-1-ol (30069-65-9) → 3,3'-diphenyl-<2,2'-binaphthalene>-1,1'-diol (587833-37-2,147702-13-4,147702-14-5)

Guidance literature:

In mineral oil; for 24h; Heating;

DOI:10.1021/op200088b

Reference yield: 2.5%

3-phenylnaphthalen-1-ol (30069-65-9) → 3,3'-diphenyl-<2,2'-binaphthalene>-1,1'-diol (587833-37-2,147702-13-4,147702-14-5) + 6,7-Diphenyl-dinaphtho[1,2-b;2',1'-d]furan

Guidance literature:

at 190 - 200 ℃; for 32h;

DOI:10.1021/ja952018t

Reference yield:

4-chloronaphthalen-1-ol (604-44-4) → 3,3'-diphenyl-<2,2'-binaphthalene>-1,1'-diol (587833-37-2,147702-13-4,147702-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / benzene / Reflux; Inert atmosphere; Sealed tube

2: neat (no solvent) / 12 h / 165 °C

With aluminum (III) chloride; In benzene;

DOI:10.1002/anie.202102352

upstream raw materials:

3-phenylnaphthalen-1-ol

phenylacetylene

phenylacetyl chloride

4-chloronaphthalen-1-ol

Refernces

• 1、 Bao, Jianming,Wulff, William D.,Dominy, James B.,Fumo, Michael J.,Grant, Eugene B.,Rob, Alexander C.,Whitcomb, Mark C.,Yeung, Siu-Man,Ostrander, Robert L.,Rheingold, Arnold L.. "Synthesis, resolution, and determination of absolute configuration of a vaulted 2,2′-binaphthol and a vaulted 3,3′-biphenanthrol (VAPOL)". . p. 3392 - 3405. Retrieved 2007/10/03.