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

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

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.

Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling

A challenging direct asymmetric catalytic aerobic oxidative cross-coupling of 2-naphthylamine and 2-naphthol, using a novel CuI/SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′-disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF3 of L17 and H-1,8 of 2-naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross-coupling reaction.

The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols

A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C?C bond formation.