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

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.

Chemical Properties

white powder

General Description

6,6′-Dibromo-1,1′-bi-2-naphthol is a 1,1′-bi-2-naphthol derivative. Vibrational circular dichroism (VCD), electronic circular dichroism (ECD) and optical rotatory dispersion (ORD) spectra for the enantiomers of 6,6′-dibromo-1,1′-bi-2-naphthol have been evaluated.

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 1150311-11-7 3-(naphthalen-2-yl)naphthalen-2-ol 
• 1150311-12-8 3-(phenylethynyl)-2-naphthol 
• 30889-48-6 3‐phenylnaphthalen‐2‐ol 
• 18531-99-2 1,1’-bi-2-naphthol 
• 108-05-4 vinyl acetate 
• 79082-80-7 (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 128544-08-1 C₃₄H₂₄Br₂O₆S₂ 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 

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.

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