(R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL

Base Information

• Chemical Name: (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL
• CAS No.: 75640-69-6
• Molecular Formula: C₂₂H₁₆Br₂O₂
• Molecular Weight: 472.176
• Mol file: 75640-69-6.mol

Synonyms:1,1'-Binaphthalene,3,3'-dibromo-2,2'-dimethoxy-, (?à)-; 3,3'-Dibromo-2,2'-dimethoxy-1,1'-binaphthyl; NSC 697407

Chemical Property of (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL

Chemical Property:

• Boiling Point: 468.4±40.0 °C(Predicted)
• Flash Point: 195.2oC
• PSA: 18.46000
• Density: 1.556±0.06 g/cm3(Predicted)
• LogP: 7.20220

Purity/Quality:

99.90% ^*data from raw suppliers

3,3'-Dibromo-2,2'-dimethoxy-1,1'-binaphthalene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36-50/53
• Safety Statements: 26-60-61

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL

There total 1 articles about (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-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:

2,2'-dimethoxy-1,1'-binaphthyl (75685-01-7) → (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene (75640-69-6,75714-59-9,75714-60-2)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; bromine; Yield given. Multistep reaction; 1) 25 deg C, 3 h, ether-hexane, 2) -78 deg C, ether-hexane-pentane;

DOI:10.1021/jo00315a033

Reference yield: 97.0%

2-Methoxyphenylboronic acid (5720-06-9) + (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene (75640-69-6,75714-59-9,75714-60-2) → 2,2'-Dimethoxy-3,3'-bis-(2-methoxy-phenyl)-[1,1']binaphthalenyl

Guidance literature:

With palladium diacetate; barium dihydroxide; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80 ℃; for 2h;

DOI:10.1021/ja00083a048

Reference yield: 84.0%

1-bromo-2-isopropylbenzene (7073-94-1) + (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene (75640-69-6,75714-59-9,75714-60-2) → (S)-3,3'-bis(2-isopropylphenyl)-2,2'-dimethoxy-1,1'-binaphthalene

Guidance literature:

1-bromo-2-isopropylbenzene; With magnesium; ethylene dibromide; In diethyl ether; for 19.5h; Reflux;

(S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene; With bis(triphenylphosphine)nickel(II) chloride; In diethyl ether; for 26h; Reflux;

DOI:10.1002/anie.201300120

upstream raw materials:

2,2'-dimethoxy-1,1'-binaphthyl

Downstream raw materials:

3,3'-diphenyl-1,1'-bi-2-naphthol

(R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol

rac-3,3'-bis(2,4,6-triisopropylphenyl)-2,2'-dimethoxy-1,1'-dinaphthyl

3,3'-Bis-(3-bromo-2-hydroxy-5-methyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol

Refernces

• 1、 Zhu, S. Sherry,Cefalo, Dustin R.,La, Daniel S.,Jamieson, Jennifer Y.,Davis, William M.,Hoveyda, Amir H.,Schrock, Richard R.. "Chiral Mo-binol complexes: Activity, synthesis, and structure. Efficient enantioselective six-membered ring synthesis through catalytic metathesis". . p. 8251 - 8259. Retrieved 2007/10/03.