(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.: 75714-59-9
• Molecular Formula: C22H16 Br2 O2
• Molecular Weight: 472.176
• Hs Code.: 29093090
• Mol file: 75714-59-9.mol

Synonyms:1,1'-Binaphthalene,3,3'-dibromo-2,2'-dimethoxy-, (R)-; (R)-3,3'-Dibromo-2,2-dimethoxy-1,1'-binaphthyl

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

Chemical Property:

• Melting Point: 185 °C
• Refractive Index: 12 ° (C=1, CHCl3)
• Boiling Point: 468.4±40.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.556±0.06 g/cm3(Predicted)
• LogP: 7.20220
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: almost transparency in Chloroform

Purity/Quality:

99% ^*data from raw suppliers

(R)-3,3''-Dibtomo-2,2’-dimethoxy-1,1’-binaphthyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/37-36
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

There total 2 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: 66.0%

(R)-2,2'-dimethoxy-1,1'-dinaphthyl (35294-28-1) → (Ra)-3,3’-dibromo-2,2’-dimethoxy-1,1’-binaphthalene (75714-59-9)

Guidance literature:

(R)-2,2'-dimethoxy-1,1'-dinaphthyl; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; hexane; at 22 ℃; for 4h;

With bromine; In diethyl ether; hexane; at -40 - 22 ℃; for 8h;

DOI:10.1021/ja991432g

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: 98.0%

(Ra)-3,3’-dibromo-2,2’-dimethoxy-1,1’-binaphthalene (75714-59-9) + (2,4,6-triisopropylphenyl)magnesium bromide (108894-99-1) → (Ra)-2,2’-dimethoxy-3,3’-bis(2,4,6-triisopropylphenyl)-1,1’-binaphthalene

Guidance literature:

With bis(triphenylphosphine)nickel(II) chloride; In diethyl ether; for 16h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201303527

upstream raw materials:

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

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

Downstream raw materials:

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

(R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol

(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

Refernces

• 1、 Mechsner, Bastian,Hen?en, Birgit,Pietruszka, J?rg. "First enantioselective total synthesis of altersolanol A". supporting information. p. 7674 - 7681. Retrieved 2018/11/02.
• 2、 Knipe, Peter C.,Smith, Martin D.. "Enantioselective one-pot synthesis of dihydroquinolones via BINOL-derived Lewis acid catalysis". supporting information. p. 5094 - 5097. Retrieved 2014/07/08.