(S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL

Base Information

• Chemical Name: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL
• CAS No.: 149821-06-7
• Molecular Formula: C₂₀H₁₂Br₂O₂
• Molecular Weight: 444.122
• Mol file: 149821-06-7.mol

Synonyms:(S)-3,3'-Dibromo-1,1'-bi-2-naphthol;3,3'-Dibromo-1,1'-binaphthalene-2,2'-diol;(R)-3,3'-Dibromo-1,1'-bi-2-naphthol;(S)-(-)-3,3'-Dibromo-1,1'-bi-2-naphthol;(S)-(+)-3,3'-Dibromo-1,1'-bi-2-naphthol;

Chemical Property of (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL

Chemical Property:

• Melting Point: 256-260 °C
• Boiling Point: 469.941 °C at 760 mmHg
• Flash Point: 238.012 °C
• PSA: 40.46000
• Density: 1.761 g/cm³
• LogP: 6.59620

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-3,3′-Dibromo-1,1′-bi-2-naphthol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL

There total 12 articles about (S)-(-)-3,3'-DIBROMO-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: 100.0%

(S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene (75640-69-6,75714-59-9,75714-60-2) → (R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol (111795-43-8,149821-06-7,119707-74-3)

Guidance literature:

With boron tribromide; In dichloromethane; for 6h; Ambient temperature;

Reference yield: 82.0%

3-bromo-2-hydroxy-naphthalene-1-diazonium-betaine (33670-69-8) + 3-bromo-2-naphthol (30478-88-7) → (R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol (111795-43-8,149821-06-7,119707-74-3)

Guidance literature:

With palladium diacetate; In dichloromethane; at 20 ℃; for 36h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1007/s11426-021-1003-9

Reference yield: 67.0%

((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid 3,3'-dibromo-2'-((1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-[1,1']binaphthalenyl-2-yl ester → (R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol (111795-43-8,149821-06-7,119707-74-3)

Guidance literature:

With sodium hydroxide; In methanol; at 60 ℃; for 20h;

DOI:10.1021/jo9610927

upstream raw materials:

(S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene

(S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene

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

6-Methoxy-2-naphthol

Downstream raw materials:

trifluoro-methanesulfonic acid 3,3'-diphenyl-2'-trifluoromethanesulfonyloxy-[1,1']binaphthalenyl-2-yl ester

2,2'-bis-bromomethyl-3,3'-diphenyl-[1,1']binaphthalenyl

2,2'-dimethyl-3,3'-diphenyl-[1,1']binaphthalenyl

Refernces

• 1、 Zhao, Xiao-Jing,Li, Zi-Hao,Ding, Tong-Mei,Tian, Jin-Miao,Tu, Yong-Qiang,Wang, Ai-Fang,Xie, Yu-Yang. "Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling". supporting information. p. 7061 - 7065. Retrieved 2021/02/27.
• 2、 He, Zhen,Pulis, Alexander P.,Procter, David J.. "The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols". supporting information. p. 7813 - 7817. Retrieved 2019/05/15.