1,1'-Bi-2-naphthol

Base Information

• Chemical Name: 1,1'-Bi-2-naphthol
• CAS No.: 18531-94-7
• Deprecated CAS: 41024-90-2
• Molecular Formula: C20H14O2
• Molecular Weight: 286.33
• Hs Code.: 29071590
• 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: 18531-94-7.mol

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

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

Chemical Property:

• Appearance/Colour: white to light yellow crystal 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: 1.301 g/cm³
• LogP: 5.07120
• Storage Temp.: 2-8°C
• Solubility.: dioxane: 50 mg/mL, clear
• Water Solubility.: Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.
• 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

(R)-(+)-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 binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.

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

There total 202 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: 99.0%

(Ra)-1,1'-binaphthalene-2'-diphenylphosphinate-2-ol → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/anie.202102352

Reference yield: 96.0%

1,1'-bi-2-naphthol (602-09-5) → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Guidance literature:

1,1'-bi-2-naphthol; With copper(l) chloride; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In methanol; dichloromethane; at -20 - 20 ℃; for 24h; Inert atmosphere; Darkness;

With sodium hydrogencarbonate; In methanol; dichloromethane; water; at -20 ℃; 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:

(R)-2,2'-dimethoxy-1,1'-dinaphthyl

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

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

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

Downstream raw materials:

C₂₀H₁₄O₂*C₈H₁₁NOS

C₂₀H₁₄O₂*C₈H₁₁NOS

(E)-3-Phenyl-acrylic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester

2'-hydroxy-1,1'-binaphthalen-2-yl benzoylformate

Refernces

• 1、 Toda, Fumio,Tanaka, Koichi,Stein, Zafra,Goldberg, Israel. "Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials". . p. 5748 - 5751. Retrieved 1994.
• 2、 Heumann, Lars V.,Keck, Gary E.. "A new method for the synthesis of H4-BINOL". . p. 4725 - 4727. Retrieved 2008.
• 3、 Takemoto, Masumi,Suzuki, Yuki,Tanaka, Kiyoshi. "Enantioselective oxidative coupling of 2-naphthol derivatives catalyzed by Camellia sinensis cell culture". . p. 8499 - 8501. Retrieved 2002.
• 4、 Liu, Dejun,Shan, Zixing,Liu, Fei,Xiao, Chunguang,Lu, Guojian,Qin, Jingui. "A new and practical method for preparing enantiomerically pure [1,1′-binaphthalene]-2,2′-diol: Resolution of racemic [1,1′-binaphthalene]-2,2′-diol with threo-(1s,2s)-2-amino-1-(4-nitrophenyl)propane-1,3-diol-cyclohexanone condensate". . p. 157 - 163. Retrieved 2003.
• 5、 Zandomeneghi, Maurizio. "Photochemical activation of racemic mixtures in biological matrices". . p. 7774 - 7775. Retrieved 1991.
• 6、 Fujimoto, Yoshinori,Iwadate, Hiroshi,Ikekawa, Nobuo. "Preparation of Optically Active 2,2'-Dihydroxy-1,1'-binaphthyl via Microbial Resolution of the Corresponding Racemic Diester". . p. 1333 - 1334. Retrieved 1985.
• 7、 Periasamy, Mariappan,Venkatraman, Lakshmanan,Justin Thomas. "New Methods of Resolution and Enrichment of Enantiomeric Excesses of 1,1′-Bi-2-naphthol". . p. 4302 - 4306. Retrieved 1997.
• 8、 Schanz, Hans-Joerg,Linseis, Michael A.,Gilheany, Declan G.. "Improved resolution methods for (R,R)- and (S,S)-cyclohexane-1,2-diamine and (R)- and (S)-BINOL". . p. 2763 - 2769. Retrieved 2003.
• 9、 Min, Kil Sik,Park, Mi Jung,Ryoo, Jae Jeong. "Synthesis and chiral recognition of nickel(II) macrocyclic complex with (R)-naphthylethyleneamine pendant groups and its self-assembled framework". . p. 54 - 58. Retrieved 2013.
• 10、 Shamoto, Taiki,Tasaki, Yuiko,Okada, Tetsuo. "Chiral ice chromatography". . p. 13135 - 13137. Retrieved 2010.