75640-87-8

Basic information

• Product Name: (S)-(-)-2,2'-Dimethoxy-1,1'-binaphthalene
• Synonyms: (S)-(-)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(S)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(S)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(S)-(-)-1,1'-BI-2-NAPHTHOL DIMETHYL ETHER;(S)-1,1'-BI-2-NAPHTHOL DIMETHYL ETHER;(R)-(+)-2,2'-DIMETHOXY-1,1'-BI-NAPHTHOL;(R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(R)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL
• CAS NO: 75640-87-8
• Molecular Formula: C₂₂H₁₈O₂
• Molecular Weight: 314.38
• Product Categories: API intermediates
• Mol File: 75640-87-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: 227-231 °C(lit.)
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble
• BRN: 4704232
• CAS DataBase Reference: (S)-(-)-2,2'-Dimethoxy-1,1'-binaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2,2'-Dimethoxy-1,1'-binaphthalene(75640-87-8)
• EPA Substance Registry System: (S)-(-)-2,2'-Dimethoxy-1,1'-binaphthalene(75640-87-8)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-50/53-37/38
• Safety Statements: 26-36/39-60-61-36
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 75640-87-8(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

Upstream product

• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 77-78-1 dimethyl sulfate 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 104116-17-8 2-methoxynaphthalene-1-boronic acid 
• 602-09-5 (-)-2,2'-dihydroxy-1,1'-binaphthyl 
• 18531-94-7 (+)-2,2'-dihydroxy-1,1'-binaphthyl 
• 13101-92-3 1-chloro-2-methoxynaphthalene 
• 32721-21-4 1-iodo-2-methoxynapthalene 
• 269410-05-1 2-(2-methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Downstream Products

• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 791616-60-9 (S)-3,3'-bis(4-nitrophenyl)-1,1'-binaphthalene-2,2'-diol 

Relevant articles and documents

Enhancing the enantioselective recognition and sensing of chiral anions by halogen bonding

Chiral halogen bonding (S)-BINOL-based receptors are demonstrated to enhance the enantioselective recognition and sensing of chiral anions compared to their hydrogen bonding analogues. Computational studies attribute this behaviour to the strict linearity of halogen bonding (XB) and steric environment conferred by the XB donor groups bridged by the (S)-BINOL motif.

A Chiral, Dendralenic C-H Acid

We report the synthesis of a chiral dendralenic C H acid, which contains three unsubstituted binaphthyl moieties. This motif and an achiral variant can be made from their corresponding bis(sulfone) precursors in one step. Despite the presence of the enantiopure binaphthyl backbone, the newly designed chiral C H acid showed only poor enantioselectivity in a Mukaiyama aldol reaction. First attempts toward the synthesis of 3,3'-hexasubstituted binaphthyl-based dendralenic acids are also reported.

Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.

Synthesis of Chiral 3,3?-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity

Abstract: A new series of 3,3?-disubstituted chiral (S)-BINOL derivatives 6a–6k has been synthesized viathe Kumada and Suzuki–Miyaura coupling reactions using (S)-BINOL as the initial compound. The Kumada coupling has beenfound to be superior in terms of