75685-01-7

Basic information

• Product Name: (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL
• Synonyms: (R)-(+)-1,1'-BI-2-NAPHTHOL DIMETHYL ETHER;(R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(R)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(R)-(+)-2,2'-DIMETHOXY-1,1'-BI-NAPHTHOL;(S)-(-)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(S)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;(S)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL;2,2'-DIMETHOXY-1,1'-BINAPHTHALENE
• CAS NO: 75685-01-7
• Molecular Formula: C₂₂H₁₈O₂
• Molecular Weight: 314.38
• Mol File: 75685-01-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 227-231 °C(lit.)
• Appearance: /
• CAS DataBase Reference: (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL(75685-01-7)
• EPA Substance Registry System: (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL(75685-01-7)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41
• Safety Statements: 26-36/39-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 75685-01-7(Hazardous Substances Data)

Usage

General Description

(R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL is a chiral compound that belongs to the class of binaphthyl compounds. It is widely used as a chiral ligand in asymmetric synthesis and catalysis reactions. (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL is known for its ability to form complexes with metal ions, which can then be used as catalysts in various chemical transformations. Its unique structure and chirality make it a valuable tool in the synthesis of pharmaceuticals, agrochemicals, and other important organic compounds. Additionally, (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL has been studied for its potential in optical and electronic applications due to its unique optical properties. Overall, this compound is an important and versatile molecule in the field of organic chemistry and materials science.

Upstream product

• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 73183-34-3 bis(pinacol)diborane 
• 602-09-5 (-)-2,2'-dihydroxy-1,1'-binaphthyl 
• 77-78-1 dimethyl sulfate 
• 18531-94-7 (+)-2,2'-dihydroxy-1,1'-binaphthyl 
• 591-50-4 iodobenzene 
• 104116-17-8 2-methoxynaphthalene-1-boronic acid 
• 93-04-9 2-Methoxynaphthalene 
• 32721-21-4 1-iodo-2-methoxynapthalene 

Downstream Products

• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 287111-93-7 3,3'-diiodo-[1,1'-binaphthalene]-2,2'-diol 
• 93-04-9 2-Methoxynaphthalene 
• 194-63-8 dinaphtho[2,1-b;1',2'-d]furan 
• 74866-27-6 (±)-6,6′-dibromo-2,2′-dimethoxy-1,1′-binaphthalene 

Relevant articles and documents

Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides

Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.

Ferrocenyl phosphine-oxazaphospholidine oxide ligands for the Suzuki-Miyaura coupling of hindered aryl bromides and chlorides

A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki-Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)2, while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.

Spontaneous Resolution of 2,2'-Dimethoxy-1,1'-binaphthalene

The dimethyl ether of 1,1'-bi-2-naphthol crystallizes as a conglomerate and can be resolved without chiral auxiliaries by entrainment.The direct crystallization of a supersaturated solution of the title compound partially enriched by one enantiomer (ee ca. 2percent) is conducted in anisole at 40 deg C and gives, after one crystallization, a compound with ee >98percent.Demethylation under nonracemizing conditions gives the enantiomeric 1,1'-bi-2-naphthol.