149821-06-7

Basic information

• Product Name: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL
• Synonyms: 3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL;3,3-DIBROMO-1,1'-BI-2-NAPHTHOL;(R)-(+)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL;(R)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL;(R)-3,3'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL;(S)-3,3'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL;(S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL;(S)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL
• CAS NO: 149821-06-7
• Molecular Formula: C₂₀H₁₂Br₂O₂
• Molecular Weight: 444.12
• Mol File: 149821-06-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 256-260 °C
• Boiling Point: 469.941 °C at 760 mmHg
• Flash Point: 238.012 °C
• Appearance: /
• Density: 1.761 g/cm³
• 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(149821-06-7)
• EPA Substance Registry System: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL(149821-06-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 149821-06-7(Hazardous Substances Data)

Usage

General Description

(S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL is a chemical compound that is used in organic synthesis and as a chiral auxiliary in asymmetric synthesis. It is a brominated derivative of 1,1'-bi-2-naphthol, and its (S)-enantiomer is the most commonly used form. (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL has a wide range of applications, including in the pharmaceutical industry as a building block for the synthesis of chiral drugs and in the production of chiral ligands for asymmetric catalysis. It is also used in the synthesis of chiral auxiliaries and ligands for enantioselective transformations. In addition, it is used in the preparation of optically active α,α-dibromo-1,2-diols, which are important intermediates in organic synthesis.

Upstream product

• 75640-69-6 (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 
• 581-71-5 2-Hydroxy-3-naphthaldehyde 
• 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 
• 33670-69-8 3-bromo-2-hydroxy-naphthalene-1-diazonium-betaine 
• 1092455-29-2 3-(benzyloxy)naphthalen-2-amine 

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

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields.

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.