119707-74-3

Basic information

• Product Name: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL
• Synonyms: (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;(R)-3,3'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL;(R)-(+)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL;(R)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL;3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL;3,3-DIBROMO-1,1'-BI-2-NAPHTHOL
• CAS NO: 119707-74-3
• Molecular Formula: C₂₀H₁₂Br₂O₂
• Molecular Weight: 444.12
• Product Categories: chiral;Asymmetric Synthesis;Synthetic Organic Chemistry;BINOLs;Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes;BINOL Series;Chiral Oxygen
• Mol File: 119707-74-3.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: White to brown/Powder
• Density: 1.761 g/cm³
• Storage Temp.: Keep in dark place,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(119707-74-3)
• EPA Substance Registry System: (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL(119707-74-3)

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: 119707-74-3(Hazardous Substances Data)

Usage

Reaction

Ligand used to prepare a chiral zirconium catalyst useful in asymmetric Strecker reactions. Ligand used in the zinc-catalyzed enantioselective Hetero Diels-Alder reaction. Catalyst used in syn-selective diastereoselective Petasis reactions. Catalyst used in asymmetric propargylation of ketones.

Chemical Properties

white to light yellow crystal powde

General Description

(S)-(-)-3,3′-Dibromo-1,1′-bi-2-naphthol may be used as a catalyst in the preparation of (R)-1-(2-propenyl)-2-(3-phenoxymethoxypropyl)-2-cyclohexenol.

Upstream product

• 75640-69-6 (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene 
• 30478-88-7 3-bromo-2-naphthol 
• 7260-11-9 phenyl 2-hydroxy-3-naphthoate 
• 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 
• 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 

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.