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

Description

(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL, also known as 2,2′-Bis(methoxymethoxy)-1,1′-binaphthalene, is an aryl alkyl ether with a unique molecular structure. It is characterized by its ability to undergo nickel-catalyzed cross-coupling reactions with aryl Grignard reagents, leading to the formation of aryl-aryl cross-coupling products. This property makes it a valuable compound in the field of organic chemistry and material science.

Uses

Used in Organic Chemistry:
(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is used as a key intermediate in the synthesis of various complex organic molecules. Its ability to participate in nickel-catalyzed cross-coupling reactions with aryl Grignard reagents allows for the creation of a wide range of aryl-aryl cross-coupling products, which are essential in the development of new pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is used as a building block for the development of novel drugs. Its unique structure and reactivity enable the synthesis of new drug candidates with potential applications in various therapeutic areas, such as oncology, neurology, and cardiovascular diseases.
Used in Material Science:
(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is also utilized in the field of material science for the development of advanced materials with specific properties. Its aryl-aryl cross-coupling capability allows for the creation of new materials with tailored electronic, optical, and mechanical properties, which can be applied in various industries, such as electronics, energy, and aerospace.

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

• 142010-87-5 (S)-3,3’-dibromo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 
• 189518-78-3 (S)-2,2’-bis(methoxymethoxy)-3,3’-diiodo-1,1’-binaphthalene 
• 142010-85-3 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl 
• 309269-73-6 (S)-3,3′-bis[hydroxy(diphenyl)methyl]-1,1′-binaphthalene-2,2′-diol 
• 863555-82-2 C₅₁H₄₁NO₄ 
• 863555-93-5 benzyl-bis-[2-(2,2'-bis-methoxymethoxy-[1,1']binaphthalenyl-3-yl)-ethyl]-amine 

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.