79082-80-7

Basic information

• Product Name: (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl
• Synonyms: (S)-6,6'-dibromo-1,1'-binaphth-2-ol
• CAS NO: 79082-80-7
• Molecular Formula: C₂₀H₁₂Br₂O₂
• Molecular Weight: 444.11608
• Mol File: 79082-80-7.mol
• Article Data: 68

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl(79082-80-7)
• EPA Substance Registry System: (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl(79082-80-7)

Safety Data

• Hazardous Substances Data: 79082-80-7(Hazardous Substances Data)

Usage

General Description

(S)-6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl is a chiral compound that consists of a binaphthyl core with two hydroxyl groups and two bromine atoms. It is commonly used as a ligand in asymmetric synthesis and catalysis due to its unique stereochemistry and reactivity. (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl has been extensively studied for its ability to form complexes with various metal ions, leading to the development of new catalysts for a wide range of organic reactions. Its chiral structure allows for precise control over the stereochemistry of the resulting products, making it a valuable tool in the synthesis of pharmaceuticals and other fine chemicals. Additionally, (S)-6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl has also been investigated for its potential biological activities and applications in material science.

Upstream product

• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 16239-18-2 1,6-dibromo-2-naphthol 
• 135-19-3 β-naphthol 
• 108-05-4 vinyl acetate 
• 30889-48-6 3‐phenylnaphthalen‐2‐ol 
• 1150311-12-8 3-(phenylethynyl)-2-naphthol 
• 1150311-11-7 3-(naphthalen-2-yl)naphthalen-2-ol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 30478-88-7 3-bromo-2-naphthol 

Downstream Products

• 13185-00-7 (+)-6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthalene 
• 13185-00-7 (S)-6,6'-dibromo-1,1'-bi-2-naphthol 
• 65283-60-5 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 
• 1006378-61-5 (6'-bromo-2,2'-dihydroxy-1,1'-binaphthyl-6-yl)triphenylphosphonium bromide 
• 1072448-36-2 C₄₀H₃₄O₆ 
• 1312293-41-6 2'-(benzyloxy)-6,6'-bis(4-(diphenylamino)phenyl)-1,1'-binaphthyl-2-ol 
• 1312293-43-8 2'-(benzyloxy)-6,6'-dibromo-1,1'-binaphthyl-2-ol 
• 1312293-42-7 2,2'-bis(benzyloxy)-6,6'-bis(4-(diphenylamino)phenyl)-1,1'-binaphthyl 
• 1312293-40-5 6,6'-bis(4-(diphenylamino)phenyl)-1,1'-binaphthyl-2,2'-diol 

Relevant articles and documents

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

Resolution of Vaulted Biaryl Ligands via Borate Esters of Quinine and Quinidine

Given the sudden and unexplained rise in the cost of (+)- A nd (-)-sparteine, an alternative method for the resolution of vaulted biaryls has been developed. This method involves the reaction of a racemic vaulted biaryl ligand with one equivalent of BH3·SMe2 and one equivalent of either quinine or quinidine. A precipitate then forms from the resulting mixture of diastereomeric borates as a result of differential solubilities. Hydrolysis of the precipitate then liberates the (S)-ligand in the case of quinine and the (R)-ligand in the case of quinidine, both with >99% ee. This method has been applied to 16 different vaulted biaryl ligands, including 10 whose preparation is described here for the first time. In addition, proof of principle has been demonstrated for the dynamic thermodynamic resolution of the vaulted biaryl ligands with this method in combination with a nonchiral copper(II) complex that can racemize the ligand.

Enantioselective iron/bisquinolyldiamine ligand‐catalyzed oxidative coupling reaction of 2‐naphthols

An iron‐catalyzed asymmetric oxidative homo‐coupling of 2‐naphthols for the synthesis of 1,1′‐Bi‐2‐naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron‐complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)‐N1,N2‐di(quinolin‐8‐yl)cyclohexane‐1,2‐diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.