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

Description

(S)-6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl is a chiral compound characterized by a binaphthyl core with two hydroxyl groups and two bromine atoms. It is distinguished by its unique stereochemistry and reactivity, which makes it a versatile and valuable compound in various fields.

Uses

Used in Asymmetric Synthesis and Catalysis:
(S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl is used as a ligand in asymmetric synthesis and catalysis for its ability to provide precise control over the stereochemistry of the resulting products. This makes it a crucial component in the synthesis of pharmaceuticals and other fine chemicals, where stereoselectivity is of utmost importance.
Used in the Development of New Catalysts:
In the field of catalysis, (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl is used as a key component in the development of new catalysts for a wide range of organic reactions. Its interaction with various metal ions allows for the formation of complexes that can enhance the efficiency and selectivity of these reactions.
Used in Material Science:
(S)-6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl is also investigated for its potential applications in material science. Its unique structural features and reactivity make it a promising candidate for the development of new materials with specific properties.
Used in Biological Activities Research:
Furthermore, (S)-6,6'-dibroMo-2,2'-dihydroxy-1,1'-binaphthyl has been explored for its potential biological activities. Its interactions with biological systems could lead to the discovery of new therapeutic applications or contribute to the understanding of biological processes at the molecular level.

Upstream product

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

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 
• 6968-28-1 4-bromophthalic acid 
• 65283-60-5 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 

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

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.

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.