13185-00-7

Basic information

• Product Name: (S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
• Synonyms: 6,6'-Dibromo-1,1'-binaphthalene-2,2'-diol;6,6'-Dibromo-2,2'-dihydroxy-1,1'-binaphthalene;6,6'-Dibromo-1,1'-bi-2-naphthol 97%;AURORA KA-7214;(+/-)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL;6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL;(+/-)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL;6'-DIBROMO-1,1'-BI-2-NAPHTHOL
• CAS NO: 13185-00-7
• Molecular Formula: C₂₀H₁₂Br₂O₂
• Molecular Weight: 444.12
• Product Categories: BINOL Series;Achiral Oxygen;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 13185-00-7.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/Powder
• Density: 1.761
• Refractive Index: 1.4947 (estimate)
• Storage Temp.: 2-8°C
• 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(13185-00-7)
• EPA Substance Registry System: (S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL(13185-00-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 13185-00-7(Hazardous Substances Data)

Usage

Description

(S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL, also known as 6,6′-Dibromo-1,1′-bi-2-naphthol, is a 1,1′-bi-2-naphthol derivative characterized by the presence of two bromine atoms at the 6,6' positions. It is a white powder with distinct chiroptical properties, as evidenced by the evaluation of its vibrational circular dichroism (VCD), electronic circular dichroism (ECD), and optical rotatory dispersion (ORD) spectra for its enantiomers.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique stereochemistry and chemical properties make it a valuable component in the development of new drugs with improved efficacy and selectivity.
Used in Chemical Synthesis:
In the field of organic chemistry, (S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL serves as an important intermediate for the synthesis of complex organic molecules. Its reactivity and structural features facilitate the creation of novel compounds with potential applications in various industries.
Used in Analytical Chemistry:
(S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL is utilized as a chiral reference standard in analytical chemistry. Its distinct chiroptical properties, such as VCD, ECD, and ORD, make it a useful tool for studying the stereochemistry of other compounds and for developing methods to determine enantiomeric purity.
Used in Materials Science:
(S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL is employed in the development of new materials with specific optical, electronic, or structural properties. Its unique molecular structure and chiroptical properties can contribute to the creation of advanced materials for various applications, such as sensors, optoelectronics, or nanotechnology.

Reactions

1. Ligand (enantiopure version) used to prepare a chiral zirconium catalyst useful in asymmetric Strecker and Mannich-type reactions. 2. Ligand (enantiopure version) used for titanium-catalyzed enantioselective Friedel-Crafts reactions.

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 108-05-4 vinyl acetate 
• 79082-80-7 (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 
• 18531-99-2 1,1’-bi-2-naphthol 
• 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 

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.