7260-11-9

Usage

Uses

Used in Chemical Synthesis Industry:
PHENYL 3-HYDROXY-2-NAPHTHOATE is used as a key intermediate for the synthesis of azoic coupling components and derivatives of naphthol AS, which are essential in the production of dyes and pigments for various applications, including textiles, plastics, and printing inks. Its unique chemical structure allows for the creation of a wide range of colors and properties in the final products.

InChI:InChI=1/C17H12O3/c18-16-11-13-7-5-4-6-12(13)10-15(16)17(19)20-14-8-2-1-3-9-14/h1-11,18H

Upstream product

• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 108-95-2 phenol 

Downstream Products

• 109689-95-4 3-acetoxy-[2]naphthoic acid phenyl ester 
• 170889-47-1 diphenyl 2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylate 
• 79044-29-4 7,7'-dimethoxy-1,1'-binaphthalene-2,2'-diol 
• 18515-12-3 3,3'-dimethoxy-1,1'-binaphthyl-2,2'-diol 
• 602-09-5 1,1'-bi-2-naphthol 
• 223903-31-9 3,3'-bis(benzyloxy)-1,1'-binaphthalene-2,2'-diol 
• 141779-46-6 2,2’-dihydroxy-[1,1’-binaphthalene]-3,3’-dicarbaldehyde 

Relevant academic research and scientific papers

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.

Nickel-Catalyzed Directed Cross-Electrophile Coupling of Phenolic Esters with Alkyl Bromides

Herein, we demonstrate the successful use of robust phenolic esters as an electrophilic acyl source in the reaction with diverse primary and secondary unactivated alkyl bromides. The cleavage of the relatively inert C-O bond is facilitated by the neighboring coordinating hydroxyl or sulfonamide moiety. By circumventing the use of pregenerated organometallics, this method allows efficient preparation of a variety of o-hydroxyl and tosyl-protected o-amino aryl ketones with high compatibility with a wide range of functionalities.

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.