75714-59-9

Basic information

• Product Name: (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL
• Synonyms: (R)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL DIMETHYL ETHER;(S)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(S)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL DIMETHYL ETHER;3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL DIMETHYL ETHER;3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(R)-3 3'-DIBROMO-2 2'-DIMETHOXY-1 1'-BI&;(R)-3,3'-Dibromo-2,2'-dimethoxy-1,1'-binaphthyl;(R)-3,3'-(R)-3,3'-Dibromo-2,2'-Dimethoxy-1-Binaphthyl
• CAS NO: 75714-59-9
• Molecular Formula: C₂₂H₁₆Br₂O₂
• Molecular Weight: 472.17
• Product Categories: chiral;Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 75714-59-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 185 °C
• Boiling Point: 468.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.556±0.06 g/cm3(Predicted)
• Refractive Index: 12 ° (C=1, CHCl3)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: almost transparency in Chloroform
• CAS DataBase Reference: (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL(75714-59-9)
• EPA Substance Registry System: (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL(75714-59-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/37-36
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 75714-59-9(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Upstream product

• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 

Downstream Products

• 75640-70-9 3,3'-diphenyl-1,1'-bi-2-naphthol 
• 75684-93-4 (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol 
• 111795-43-8 (R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol 
• 630126-21-5 rac-3,3'-bis(2,4,6-triisopropylphenyl)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 148950-84-9 3,3'-Bis-(3-bromo-2-hydroxy-5-methyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol 
• 148951-16-0 3,3'-Bis-[3-bromo-2-(tert-butyl-diphenyl-silanyloxy)-5-methyl-phenyl]-[1,1']binaphthalenyl-2,2'-diol 
• 148950-85-0 3,3'-Bis-(3-bromo-5-methyl-2-triphenylsilanyloxy-phenyl)-[1,1']binaphthalenyl-2,2'-diol 
• 148950-90-7 3,3'-Bis-(3-bromo-5-methyl-2-tri-o-tolylsilanyloxy-phenyl)-[1,1']binaphthalenyl-2,2'-diol 
• 142823-16-3 C₆₀H₄₆N₄O₁₁ 

Relevant articles and documents

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields.

Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC

Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3'-halogen substituted-1,1'-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one α-amino acids have different degrees of separation on R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1'-binaphthyl)-20-crown-6 derivatives. Both the separation factors (α) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 chiral stationary phase.

Catalytic enantioselective amination of alcohols by the use of borrowing hydrogen methodology: Cooperative catalysis by iridium and a chiral phosphoric acid

The catalytic asymmetric reduction of ketimines has been explored extensively for the synthesis of chiral amines, with reductants ranging from Hantzsch esters, silanes, and formic acid to H2 gas. Alternatively, the amination of alcohols by the use of borrowing hydrogen methodology has proven a highly atom economical and green method for the production of amines without an external reductant, as the alcohol substrate serves as the H2 donor. A catalytic enantioselective variant of this process for the synthesis of chiral amines, however, was not known. We have examined various transition- metal complexes supported by chiral ligands known for asymmetriC-Hydrogenation reactions, in combination with chiral Bronsted acids, which proved essential for the formation of the imine intermediate and the transfer-hydrogenation step. Our studies led to an asymmetric amination of alcohols to provide access to a wide range of chiral amines with good to excellent enantioselectivity.