111795-43-8

Basic information

• Product Name: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL
• Synonyms: (R)-3,3′-Dibromo-[1,1′-Binaphthalene]-2,2′-diol;(R)-Dibromo-1,1′-Bi-2,2′-naphthol;(R)-Dibromo-1,1′-Binaphthalene-2,2′-diol;(R)-Dibromo-1,1-Binaphthol;(R)-Dibromo-bi-2-naphthol;(R)-Dibromo-BINOL;(R)-(+)-3,3'-Dibromo-1,1'-bi-2-naphthol 97%;(R)-3,3'-Dibromo-1,1'-bi-2-naphthol, 99%e.e.
• CAS NO: 111795-43-8
• Molecular Formula: C₂₀H₁₂Br₂O₂
• Molecular Weight: 444.12
• Product Categories: BINOL Series;Chiral Oxygen;chiral;Asymmetric Synthesis;Synthetic Organic Chemistry;BINOLs;Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes
• Mol File: 111795-43-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 256-260 °C
• Boiling Point: 469.9 °C at 760 mmHg
• Flash Point: 238 °C
• Appearance: White to pale yellow-beige/Powder
• Density: 1.761 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.779
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: within almost transparency in Methanol
• PKA: 6.43±0.50(Predicted)
• CAS DataBase Reference: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL(111795-43-8)
• EPA Substance Registry System: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL(111795-43-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-37/39
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 111795-43-8(Hazardous Substances Data)

Usage

Description

(S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL is a chiral organic compound that exists as a white to light yellow crystalline powder. It is characterized by its unique molecular structure, featuring two naphthol moieties connected by a methylene bridge and substituted with bromine atoms at the 3,3' positions. (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL is known for its potential applications in various chemical and industrial processes due to its distinct chemical properties.

Uses

Used in Chiral Catalysts:
(S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL is used as a chiral ligand in the synthesis of chiral zirconium complexes. These complexes are highly efficient catalysts for enantioselective catalytic asymmetric aldol reactions of silyl enol ethers with aldehydes. The chiral centers present in the compound contribute to the selectivity and efficiency of the catalytic process, making it a valuable component in the development of enantioselective catalysts.
Used in Cycloaddition Reactions:
In the field of organic synthesis, (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL is utilized as a precursor in the asymmetric intramolecular [3+2] cycloaddition of hydrazone/olefins. This reaction is an important method for the construction of complex molecular architectures and the synthesis of biologically active compounds. The chiral nature of the compound plays a crucial role in determining the stereochemistry of the final product, making it a valuable building block in the synthesis of enantioselective compounds.
Used in Pharmaceutical Industry:
(S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL can be employed as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and chiral properties make it a promising candidate for the development of novel drugs with improved efficacy and selectivity. (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL can be further modified and functionalized to create new drug molecules with specific therapeutic properties.
Used in Chemical Synthesis:
(S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL is also used as a versatile building block in the synthesis of various organic compounds. Its reactivity and functional groups can be exploited in various chemical reactions, such as cross-coupling, oxidation, and reduction, to generate a wide range of products with diverse applications in materials science, agrochemicals, and other industries.

InChI:InChI=1/C20H12Br2O2/c21-15-9-11-5-1-3-7-13(11)17(19(15)23)18-14-8-4-2-6-12(14)10-16(22)20(18)24/h1-10,23-24H

Upstream product

• 1092455-29-2 3-(benzyloxy)naphthalen-2-amine 
• 30478-88-7 3-bromo-2-naphthol 
• 7260-11-9 phenyl 2-hydroxy-3-naphthoate 
• 17295-11-3 methyl 6-hydroxynaphthalene-2-carboxylate 
• 5111-66-0 6-Methoxy-2-naphthol 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 75714-60-2 (S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene 
• 75640-69-6 (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene 
• 33670-69-8 3-bromo-2-hydroxy-naphthalene-1-diazonium-betaine 
• 581-71-5 2-Hydroxy-3-naphthaldehyde 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 

Downstream Products

• 326793-10-6 trifluoro-methanesulfonic acid 3,3'-diphenyl-2'-trifluoromethanesulfonyloxy-[1,1']binaphthalenyl-2-yl ester 
• 237753-18-3 2,2'-bis-bromomethyl-3,3'-diphenyl-[1,1']binaphthalenyl 
• 326793-12-8 2,2'-dimethyl-3,3'-diphenyl-[1,1']binaphthalenyl 

Relevant articles and documents

A versatile method for the resolution and absolute configuration assignment of substituted 1,1′-Bi-2-naphthols

-

Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones

Privileged biaryl frameworks, BINOL and NOBIN, were efficiently constructed with sole 1-DNQs as arylation reagents under one set of reaction conditions. The judicious selection of palladium-catalytic system plays a pivotal role in the excellent selectivities. This transformation accommodated fairly broad substrate generality for both 2-naphthol and N-Boc-2-naphthylamine and afforded the structurally diversified BINOLs and NOBIN derivatives in high efficiency. Notably, the bromo-substituents which cannot survive in conventional palladium-catalyzed reactions were well-compatible with this set of conditions, providing an effective handle for further enriching the library of BINOLs and NOBINs. Preliminary attempts on the asymmetric variant of this reaction were also performed with up to 80:20 er for BINOLs synthesis. [Figure not available: see fulltext.].

Copper-Complex-Catalyzed Asymmetric Aerobic Oxidative Cross-Coupling of 2-Naphthols: Enantioselective Synthesis of 3,3′-Substituted C1-Symmetric BINOLs

A novel chiral 1,5-N,N-bidentate ligand based on a spirocyclic pyrrolidine oxazoline backbone was designed and prepared, and it coordinates CuBr in situ to form an unprecedented catalyst that enables efficient oxidative cross-coupling of 2-naphthols. Air serves as an external oxidant and generates a series of C1-symmetric chiral BINOL derivatives with high enantioselectivity (up to 99 % ee) and good yield (up to 87 %). This approach is tolerant of a broader substrates scope, particularly substrates bearing various 3- and 3′-substituents. A preliminary investigation using one of the obtained C1-symmetric BINOL products was used as an organocatalyst, exhibiting better enantioselectivity than the previously reported organocatalyst, for the asymmetric α-alkylation of amino esters.