791616-60-9

Basic information

• Product Name: R-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol
• Synonyms: R-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol;(R)-3,3'-Bis(4-nitrophenyl)-[1,1'-binapthalene]-2,2'-diol
• CAS NO: 791616-60-9
• Molecular Formula: C32H20N2O6
• Molecular Weight: 528.53
• Mol File: 791616-60-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: R-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: R-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol(791616-60-9)
• EPA Substance Registry System: R-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol(791616-60-9)

Safety Data

• Hazardous Substances Data: 791616-60-9(Hazardous Substances Data)

Usage

General Description

R-3,3'-bis(4-nitrophenyl)-1,1'-Binaphthalene]-2,2'-diol, also known as BINAPO, is an organic compound used as a chiral ligand in asymmetric catalysis. It is a bifunctional molecule with two 1,1'-binaphthyl units connected by a central 2,2'-diol group. BINAPO has a high affinity for transition metals such as palladium, rhodium, and ruthenium, making it suitable for use in a variety of asymmetric catalytic reactions. Its unique structure and ability to form stable complexes with metals have made BINAPO a valuable tool in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals.

Upstream product

• 602-09-5 1,1'-bi-2-naphthol 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 75714-60-2 (S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 586-78-7 para-nitrophenyl bromide 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 

Relevant articles and documents

Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol

The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.

Rapid synthesis of 3,3′ bis-arylated BINOL derivatives using a C-H borylation in situ suzuki-miyaura coupling sequence

The increased interest in BINOL derived catalysts for asymmetric transformations has encouraged us to disclose a rapid and scalable method of preparing 3,3′ bis-arylated BINOL derivatives 1 using a one-pot CH borylation/Suzuki-Miyaura coupling sequence. T

Chiral Bronsted acid catalyzed enantioselective Mannich-type reaction

Mannich-type reaction of ketene silyl acetals with aldimines proceeded catalytically by means of a phosphoric acid diester, derived from (R)-BINOL, as a chiral Bronsted acid to afford β-amino esters with good diastereoselectivity in favor of the syn isomer and high enantioselectivity (up to 96% ee). The highest enantioselectivity was achieved by the phosphoric acid diester bearing 4-nitrophenyl groups on the 3,3′-positions of BINOL. The N-2-hydroxyphenyl group of aldimine was found to be essential for the present Mannich-type reaction. In combination with these experimental investigations, two possible monocoordination and dicoordination pathways were explored using density functional theory calculations (BHandHLYP/6-31G*). The present reaction proceeds via a dicoordination pathway through the zwitterionic and nine-membered cyclic transition state (TS) consisting of the aldimine and the phosphoric acid. The re-facial selectivity was also well-rationalized theoretically. The nine-membered cyclic structure and aromatic stacking interaction between the 4-nitrophenyl group and N-aryl group would fix the geometry of aldimine on the transition state, and the si-facial attacking TS is less favored by the steric hindrance of the 3,3′-aryl substituents.