(S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl

Base Information

• Chemical Name: (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl
• CAS No.: 79082-80-7
• Molecular Formula: C20H12Br2O2
• Molecular Weight: 444.122
• Mol file: 79082-80-7.mol

Synonyms:(S)-6,6'-dibromo-1,1'-binaphth-2-ol

Chemical Property of (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl

Chemical Property:

• Melting Point: 198 - 200 °C
• PSA: 40.46000
• LogP: 6.59620

Purity/Quality:

97-99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl

There total 17 articles about (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl 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: 100.0%

(S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) → (S)-6,6'-dibromo-1,1'-bi-2-naphthol (13185-00-7,65283-60-5,79082-80-7,80655-81-8)

Guidance literature:

With bromine; In dichloromethane; at -78 ℃; Inert atmosphere;

Reference yield: 48.0%

(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol (79082-80-7) → (R)-6,6'-dibromo-1,1'-binaphth-2-ol (65283-60-5) + (S)-6,6'-dibromo-1,1'-bi-2-naphthol (13185-00-7,65283-60-5,79082-80-7,80655-81-8)

Guidance literature:

(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol; With dimethylsulfide borane complex; In tetrahydrofuran; toluene; at 80 ℃; for 0.5h; Inert atmosphere;

With quinidine; In tetrahydrofuran; hexane; at 80 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In water; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.joc.0c00494

Reference yield: 47.0%

3‐phenylnaphthalen‐2‐ol (30889-48-6) + 3-bromo-2-naphthol (30478-88-7) → (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol (79082-80-7) + 3-bromo-3'-phenyl-1,1'-bi-2,2'-naphthol + 3,3'-diphenyl-1,1'-bi-2-naphthol (75640-70-9,75684-93-4,102490-05-1)

Guidance literature:

With C₁₃₆H₁₀₂Fe₂N₄O₆; In toluene; at 60 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja105442m

upstream raw materials:

3-hydroxy-2-naphthoic acid methyl ester

6-bromo-naphthalen-2-ol

1,6-dibromo-2-naphthol

β-naphthol

Downstream raw materials:

(±)-6,6′-dibromo-2,2′-dimethoxy-1,1′-binaphthalene

(+)-6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthalene

(S)-6,6'-dibromo-1,1'-bi-2-naphthol

(R)-6,6'-dibromo-1,1'-binaphth-2-ol

Refernces

• 1、 He, Yanrong,Zhang, Shu,Bisoyi, Hari Krishna,Qiao, Jinghui,Chen, Hong,Gao, JingJing,Guo, Jinbao,Li, Quan. "Irradiation-Wavelength Directing Circularly Polarized Luminescence in Self-Organized Helical Superstructures Enabled by Hydrogen-Bonded Chiral Fluorescent Molecular Switches". supporting information. p. 27158 - 27163. Retrieved 2021/10/25.
• 2、 Demaerel, Joachim,Graff, David E.,Knowles, Robert R.,Roos, Casey B.. "Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer". supporting information. p. 5974 - 5979. Retrieved 2020/04/27.