80655-81-8

Basic information

• Product Name: (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol
• Synonyms: 6'-DIBROMO-1,1'-BI-2-NAPHTHOL;(+/-)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL;(+/-)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL;6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL;AURORA KA-7214;(R)-(-)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL;(R)-(-)-6,6'-DIBROMO-1,1'-BI-NAPHTHOL;(R)-(-)-6,6'-DIBROMO 1,1'-BL-2-NAPHTHOL
• CAS NO: 80655-81-8
• Molecular Formula: C₂₀H₁₂Br₂O₂
• Molecular Weight: 444.12
• EINECS: 1592732-453-0
• Product Categories: blocks;Bromides;chiral;Asymmetric Synthesis;Synthetic Organic Chemistry;Privileged Ligands and Complexes;BINOLs;Chiral Catalysts, Ligands, and Reagents;BINOL Series;Chiral Oxygen
• Mol File: 80655-81-8.mol
• Article Data: 65

Chemical Properties

• Melting Point: 195-199 °C(lit.)
• Boiling Point: 546.2 °C at 760 mmHg
• Flash Point: 284.1 °C
• Appearance: white to light yellow crystal powder
• Density: 1.5428 (rough estimate)
• Refractive Index: 1.4947 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: slightly sol. in Tetrahydrofuran
• PKA: 7.78±0.50(Predicted)
• CAS DataBase Reference: (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol(80655-81-8)
• EPA Substance Registry System: (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol(80655-81-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 80655-81-8(Hazardous Substances Data)

Usage

Reactions

Ligand used to prepare a chiral zirconium catalyst useful in asymmetric Strecker reactions. Ligand used in the zinc-catalyzed enantioselective Hetero Diels-Alder reaction. Ligand used in asymmetric Friedel-Crafts reactions of pyrroles with glyoxylates.

Chemical Properties

white to light yellow crystal powde

Uses

(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol may be used in the synthesis of (2R,3S)-3-phenylisoserine hydrochloride. It may also be used in the synthesis of BINOL-derived chiral ligands with aryl substituents in the 6,6-positions. [BINOL=1,1′-bi-2-naphthol]

General Description

(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol is an aromatic chiral Bronsted acid.

Upstream product

• 79082-80-7 (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 108-05-4 vinyl acetate 
• 18531-99-2 1,1’-bi-2-naphthol 
• 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 

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.

Novel π-expanded chrysene-based axially chiral molecules: 1,1′-bichrysene-2,2′-diols and thiophene analogs

1,1′-Bichrysene-2,2′-diol and its thiophene analogs, 6,6′-biphenanthro-[1,2-b]thiophene-7,7′-diols, as a series of novel π-expanded chrysene-/phenanthro[1,2-b]thiophene-based axially chiral molecules are synthesized from 1,1′-bi-2-naphthols with key steps