428874-67-3

Basic information

• Product Name: R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene
• Synonyms: R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene;(R)-2,2'-Bis(methoxymethoxy)-3,3'-diphenyl-1,1'- binaphthalene,99%e.e.
• CAS NO: 428874-67-3
• Molecular Formula: C₃₆H₃₀O₄
• Molecular Weight: 526.621
• Mol File: 428874-67-3.mol

Chemical Properties

• Boiling Point: 582.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.177±0.06 g/cm3(Predicted)
• CAS DataBase Reference: R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene(428874-67-3)
• EPA Substance Registry System: R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene(428874-67-3)

Safety Data

• Hazardous Substances Data: 428874-67-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene is used as a chiral ligand for facilitating asymmetric catalysis in chemical reactions. It is instrumental in controlling the stereochemistry, leading to the production of enantiomerically pure compounds, which is crucial for the synthesis of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Development:
In the pharmaceutical industry, R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene is utilized in the development of new drugs and biologically active compounds. Its ability to influence the stereochemistry of reactions aids in creating molecules with specific biological activities, which is essential for the discovery of novel therapeutic agents.
Used in Academic Research:
R-2,2'-bis(methoxymethoxy)-3,3'-diphenyl-1,1'-Binaphthalene serves as a key research tool in academic settings, where it is employed to study the mechanisms of asymmetric catalysis and to explore new methods for the synthesis of complex organic molecules. Its unique properties make it an attractive subject for investigations into the fundamentals of stereoselective reactions and their applications in organic chemistry.

Upstream product

• 98-80-6 phenylboronic acid 
• 142010-87-5 (±)?3,3'?dibromo?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 

Downstream Products

• 75640-70-9 3,3'-diphenyl-1,1'-bi-2-naphthol 

Relevant articles and documents

Synthesis of (±)-3,3′-diphenyl-2,2′-binaphthol via different routes using Pd and Ni as catalyst respectively

3,3′-Biphenyl-2,2′-binaphthols (BINOLs) are precursors of phosphoric acids that are widely used as ligands and catalysts in organic reactions. In this report, two routes for the synthesis of (±)-3,3′-diphenyl BINOLs via (±)-3,3′ bis-halogenated BINOLs int

Asymmetric allylboration of aldehydes and ketones using 3,3′-disubstitutedbinaphthol-modified boronates

Allylboronates derived from 3,3′-disubstituted 2,2′-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness.

Design of bronsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels-Alder reactions

Bronsted acid-assisted chiral Lewis acid (BLA) was highly effective as a chiral catalyst for the enantioselective Diels-Alder reaction of both α- substituted and α-unsubstituted α,β-enals with various dienes. Hydroxy groups in optically active binaphthol derivatives and boron reagents with electron-withdrawing substituents were used as Bronsted acids and Lewis acids, respectively. Intramolecular Bronsted acids in a chiral BLA catalyst played an important role in accelerating the rate of Diels-Alder reactions and in producing a high level of enantioselectivity. In particular, excellent enantioselectivity was achieved due to intramolecular hydrogen bonding interaction and attractive π-π donor-acceptor interaction in the transition-state assembly by hydroxy aromatic groups in a chiral BLA catalyst.