1,1'-Bi-2-naphthol

Base Information

• Chemical Name: 1,1'-Bi-2-naphthol
• CAS No.: 18531-99-2
• Deprecated CAS: 41024-90-2
• Molecular Formula: C20H14O2
• Molecular Weight: 286.33
• Hs Code.: 29072990
• European Community (EC) Number: 606-050-5,210-014-0,606-048-4
• NSC Number: 27049
• UNII: M6IDZ128WT,54OT5RRV4C,25AB254328
• DSSTox Substance ID: DTXSID9060526
• Nikkaji Number: J1.031.260D,J1.031.261B,J1.055.781J,J1.055.782H,J134.638E,J166.096I,J54.937A
• Wikipedia: 1,1%E2%80%B2-Bi-2-naphthol
• Wikidata: Q161292,Q72443503,Q72443501
• ChEMBL ID: CHEMBL138718
• Mol file: 18531-99-2.mol

Synonyms:1,1'-bi-2-naphthol

Chemical Property of 1,1'-Bi-2-naphthol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 215-218 °C
• Refractive Index: -36.0 ° (C=1, THF)
• Boiling Point: 388.69°C (rough estimate)
• PKA: 8.29±0.50(Predicted)
• PSA: 40.46000
• Density: 1 g/cm³
• LogP: 5.07120
• Storage Temp.: 2-8°C
• Solubility.: dioxane: 50 mg/mL, clear
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 286.099379685
• Heavy Atom Count: 22
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-1,1'-Bi-2-naphthol >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-36-36/37/38
• Safety Statements: 26-45-24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)O)O
• Uses: Chiral ligand. (S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:asymmetric addition of alkynylzinc to unactivated ketonesenantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilinesasymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketonesIt can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.

Technology Process of 1,1'-Bi-2-naphthol

There total 164 articles about 1,1'-Bi-2-naphthol 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: 97.0%

1,1'-bi-2-naphthol (602-09-5) → (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2)

Guidance literature:

1,1'-bi-2-naphthol; With copper(l) chloride; (-)-sparteine; In methanol; dichloromethane; at 25 ℃; for 24h; Inert atmosphere; Darkness;

With hydrogenchloride; In methanol; dichloromethane; water; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja903820m

Reference yield: 95.0%

1,1'-bi-2-naphthol (602-09-5) → C20H12O3 + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2)

Guidance literature:

1,1'-bi-2-naphthol; With copper(l) chloride; (-)-sparteine; In methanol; dichloromethane; at 25 ℃; for 24h; Inert atmosphere; Darkness;

With sodium hydrogencarbonate; In methanol; dichloromethane; water; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja903820m

Reference yield: 94.0%

β-naphthol (135-19-3) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2)

Guidance literature:

With oxygen; oxovanadium(IV); In tetrachloromethane; at 20 ℃; for 144h;

DOI:10.1021/ol015505o

upstream raw materials:

2,2'-diacetoxy-1,1'-binaphthyl

1-Indanol

<1,1'-Binaphthalene>-2,2'-diol dibutanoate

<1,1'-Binaphthalene>-2,2'-diol butanoate

Downstream raw materials:

C₅₀H₄₄O₆*C₈H₉NO₂*ClHO₄

(4-Chloro-phenyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester

4-Methoxyphenylacetic acid (S)-(-)-2'-hydroxy-1,1'-binaphthyl-2-yl ester

(2-Methoxy-phenyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester

Refernces

• 1、 Miyano, Sotaro,Tobita, Masayuki,Nawa, Masayoshi,Sato, Shinya,Hashimoto, Harukichi. "Induction of Axial Dissymmetry into the 1,1'-Binaphthyl Bond via an Intramolecular Ullmann Coupling Reaction". . p. 1233 - 1234. Retrieved 1980.
• 2、 Brussee, J.,Jansen, A.C.A.. "A HIGHLY STEREOSELECTIVE SYNTHESIS OF S(-)--2,2'-DIOL.". . p. 3261 - 3262. Retrieved 1983.
• 3、 Wang, Yang,Sun, Jie,Ding, Kuiling. "Practical method and novel mechanism for optical resolution of BINOL by molecular complexation with N-benzylcinchoninium chloride". . p. 4447 - 4451. Retrieved 2000.
• 4、 Gao, Ya-Ya,Zhang, Yu-Hang,Zhang, Shan,Chen, Wei,Bai, Zheng-Wu. "Chiral separation materials based on derivatives of 6-amino-6-deoxyamylose". supporting information. p. 899 - 914. Retrieved 2021/10/07.
• 5、 Walsh, Mark P.,Phelps, Joseph M.,Lennon, Marc E.,Yufit, Dmitry S.,Kitching, Matthew O.. "Enantioselective synthesis of ammonium cations". . p. 70 - 76. Retrieved 2021/09/06.