74292-20-9

Basic information

• Product Name: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL
• Synonyms: 2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE;(S)-(-)-2,2'-BIS(METHOXYMETHOXY)-1,1-BINAPHTHALENE;(S)-(-)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(S)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(R)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE
• CAS NO: 74292-20-9
• Molecular Formula: C₂₄H₂₂O₄
• Molecular Weight: 374.43
• Mol File: 74292-20-9.mol
• Article Data: 63

Chemical Properties

• Melting Point: 92-96 °C(lit.)
• Boiling Point: 477.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.182±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL(74292-20-9)
• EPA Substance Registry System: (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL(74292-20-9)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 74292-20-9(Hazardous Substances Data)

Usage

General Description

2,2′-Bis(methoxymethoxy)-1,1′-binaphthalene is an aryl alkyl ether that can undergo nickel catalyzed cross-coupling reaction with aryl Grignard reagent to form the aryl-aryl cross-coupling product.

Upstream product

• 13057-19-7 Iodomethyl methyl ether 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 107-30-2 chloromethyl methyl ether 
• 109-87-5 Dimethoxymethane 
• 13185-00-7 (S)-6,6'-dibromo-1,1'-bi-2-naphthol 
• 602-09-5 (R)-binaphthol 

Downstream Products

• 39648-71-0 3,3’-dimethyl-[1,1’-binaphthalene]-2,2’-diol 
• 142010-87-5 (S)-3,3’-dibromo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 

Relevant articles and documents

Enantioselective Au(i)-catalyzed dearomatization of 1-naphthols with allenamides through Tethered Counterion-Directed Catalysis

The Tethered Counterion-Directed Catalysis (TCDC) approach has been applied to the enantioselective Au(i) catalyzed dearomatizations of 1-naphthols with allenamides. Stereocontrol is ensured by the intramolecular ion-pairing between the chiral gold-tether

Chiral Metallacycles as Catalysts for Asymmetric Conjugate Addition of Styrylboronic Acids to α,β-Enones

Introducing self-assembly strategies into the construction of catalysts has been proven to have great advantages in asymmetric catalysis. We constructed two chiral metalla-triangles by highly efficient coordination-driven self-assembly from a chiral 3,3′-dipyridyl-substituted BINOL donor. They were successfully applied in asymmetric conjugate addition of a series of α,β-unsaturated ketones with trans-styrylboronic acids. The use of these metalla-triangles as supramolecular catalysts is obviously conducive to the enhancement of catalytic activity and stereoselectivity in the presented addition reactions. Under induction of the chiral metalla-triangles, an array of α,β-enones were converted to chiral ?,I-unsaturated ketones in medium to quantitative yields (40-98%) with high enantioselectivities (87-96% ee).

Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs

Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.