18531-91-4

Usage

Uses

Used in Pharmaceutical Applications:
Taxifolin is used as a therapeutic agent for its potential anti-cancer properties. It is being studied for its ability to protect cells from damage, reduce inflammation, and improve cardiovascular health, making it a promising candidate for various pharmaceutical applications.
Used in Cosmetic and Skincare Industry:
In the cosmetic and skincare industry, (R)-(+)-DIMETHYL-2 2'-DIHYDROXY-1 1'-BI& is used as an active ingredient for its potential to protect the skin from UV damage and oxidative stress. Its antioxidant properties contribute to the development of skincare products that aim to maintain skin health and prevent premature aging.

Upstream product

• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 5060-82-2 7-methoxy-2-naphthol 
• 135-88-6 N-Phenyl-2-naphthylamine 
• 18515-11-2 3-methoxy-2-naphthol 
• 1081-32-9 6-t-butyl-2-naphthol 
• 17324-04-8 3-methyl-naphthalen-2-ol 
• 2038-55-3 7-Benzoyloxy-2-naphthol 
• 21597-54-6 Methyl 3-amino-2-naphthoate 
• 10155-37-0 methyl 3-hydroxy-7-methoxy-naphthalene-2-carboxylate 
• 91-59-8 naphthalen-2-ylamine 
• 67-56-1 methanol 
• 18531-92-5 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid 
• 135-19-3 β-naphthol 

Downstream Products

• 155580-25-9 2,2'-Bis<2-<2-<3-formyl-2-(2-propenyloxy)phenoxy>ethoxy>ethoxy>-<1,1'-binaphthalene>-3,3'-dicarboxylic acid dimethyl ester 
• 155580-26-0 2,2'-Bis<2-<2-<2-<3-formyl-2-(2-propenyloxy)phenoxy>ethoxy>ethoxy>ethoxy>-<1,1'-binaphthalene>-3,3'-dicarboxylic acid dimethyl ester 
• 18531-92-5 (R)-2,2'-dihydroxy-(1,1'-binaphthalene)-3,3'-dicarboxylic acid 
• 18531-92-5 (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylic acid 
• 155580-35-1 2,2'-Bis<2-<2-<3-formyl-2-hydroxyphenoxy>ethoxy>ethoxy>-N,N'-bis(2-hydroxy-5-methylphenyl)-<1,1'-binaphthalene>-3,3'-dicarboxamide 
• 155580-36-2 2,2'-Bis<2-<2-<2-<3-formyl-2-hydroxyphenoxy>ethoxy>ethoxy>ethoxy>-N,N'-bis(2-hydroxy-5-methylphenyl)-<1,1'-binaphthalene>-3,3'-dicarboxamide 
• 155580-31-7 2,2'-Bis<2-<2-<3-formyl-2-(2-propenyloxy)phenoxy>ethoxy>ethoxy>-N,N'-bis(2-hydroxy-5-methylphenyl)-<1,1'-binaphthalene>-3,3'-dicarboxamide 
• 155580-32-8 2,2'-Bis<2-<2-<2-<3-formyl-2-(2-propenyloxy)phenoxy>ethoxy>ethoxy>ethoxy>-N,N'-bis(2-hydroxy-5-methylphenyl)-<1,1'-binaphthalene>-3,3'-dicarboxamide 
• 634584-59-1 C₅₂H₃₈N₂O₁₀P₂ 
• 18531-92-5 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid 

Relevant academic research and scientific papers

A New Catalytic System for Aerobic Oxidative Coupling of 2-Naphthol Derivatives by the Use of CuCl-Amine Complex: A Practical Synthesis of Binaphthol Derivatives

Aerobic oxidative coupling of 2-naphthol derivatives by the use of 1 molpercent of CuCl-amine complex afforded binaphthol derivatives in excellent yields.

Aerobic oxidative coupling of 2-naphthoi derivatives catalyzed by a copper-amine complex without solvent

Aerobic oxidative coupling of naphthols catalyzed by a copper-amine complex was found to proceed without solvent in high efficacy. The present reaction was applied to a practical synthesis of l,l'-binaphthalene-2,2'-dio] on multi-gram scale.

Enantioselective oxidative coupling of methyl 3-hydroxy-2-naphthoate using mono-N-alkylated octahydrobinaphthyl-2,2′-diamine ligand

Mono-N-alkylated octahydrobinaphthyl-2,2′-diamine (H 8-BINAM) chiral ligands were employed in the catalytic and asymmetric oxidative coupling of methyl 3-hydroxy-2-naphthoate to the corresponding binaphthol derivative. The diamine ligand with one N-(3-pentyl) group shows highest enantioselectivity in the biaryl coupling among other BINAM derivatives, and the coupling reaction proceeds faster than the reactions using alkanediamine ligands.

Facile synthesis of BINOL in the absence of solvent

A new synthesis of BINOL is reported, which proceeds by the oxidation of 2-naphthol by iron(III) chloride when the two reagents are co-adsorbed on alumina. The method allows easy isolation of the product in high yield and in a high state of purity and does not require the use of specialized catalysts or large volumes of high-boiling organic solvents. Some derivatives of BINOL can also be prepared by this method.

Aerobic catalytic oxidative coupling of 2-naphthols and phenols by VO(acac)2

In the presence of a catalytic amount of VO(acac)2, oxidative coupling of 2-naphthol or phenol derivatives with molecular oxygen occurred at room temperature and selectively gave the corresponding ortho-ortho coupling products in moderate to high yields.

Horseradish peroxidase: An effective but unselective biocatalyst for biaryl synthesis

The oxidative dimerization of phenolic and naphtholic compounds catalyzed by horseradish peroxidase was investigated. Contrary to Sridhar et al. [Tetrahedron Lett., 1997, 38, 5695-5696] exclusively racemic biaryl compounds were identified.

Naphthol coupling monitored by infrared spectroscopy in the gas phase

The reaction mechanism of copper(II)-mediated naphthol coupling in the presence of TMEDA (N,N,N',N'-tetramethylethylenediamine) is studied using infrared multiphoton dissociation (IRMPD) spectroscopy and DFT calculations. It is shown that the coupling reaction proceeds in ad hoc formed binuclear clusters [(1-H)2Cu2Cl(TMEDA)2]+, where (1-H) is a deprotonated naphthol molecule (methyl ester of 3-hydroxy-2-naphthoic acid). The IRMPD spectra of the isolated cluster in the gas phase reveal that it contains two uncoupled naphtholate subunits and only the irradiation promotes the coupling reaction, which is thus observed as a genuine gas-phase reaction. The driving force for the C-C coupling is a keto-enol tautomerization of the initial coupling product, and the formation of the corresponding binol in the cluster is exothermic by 0.61 eV. In contrast, analogous C-O and O-O couplings are endothermic reactions.

In-depth structure-selectivity investigations on asymmetric, copper-catalyzed oxidative biaryl coupling in the presence of 5-cis-substituted prolinamines

Thirteen new and 25 known prolinamines carrying an additional 5-cis substituent were evaluated as the chiral ligands in asymmetric copper-catalyzed, oxidative biaryl coupling of 3-hydroxy-2-naphthoates. Comprehensive structure-selectivity investigations r

Accurate Understanding the Catalytic Role of MnO2 in the Oxidative-Coupling of 2-naphthols into 1,1′-bi-2-naphthols

Abstract: It has been reported that β-MnO2 has photocatalytic activity for the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols. Nevertheless, it is hard to exclude the possibility that the oxidative-coupling of 2-naphthols is initiated by β-MnO2 catalysis in dark due to the insufficient investigations in the related reports. In the present work, the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols with different phases MnO2 catalysis in dark and under visible-light irradiation were systematically investigated. The results revealed that the oxidative-coupling of 2-naphthols is jointly initiated by MnO2 catalysis and O2-oxidation, not by MnO2 photocatalysis. Among the α-MnO2, β-MnO2, γ-MnO2 and δ-MnO2 catalysis, β-MnO2 catalysis has the optimal performance, its selectivity for the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols is close to 100%, and its catalytic capacity could be well retained after multiple using. Our findings provide comprehensive and accurate understanding the catalytic role of MnO2 for the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols. Graphic Abstract: In the present work, the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols was proved to be jointly initiated by MnO2 catalysis and O2-oxidation, not by MnO2 photocatalysis. β-MnO2 has the optimal catalytic activity for the oxidative-coupling of 2-naphthols relative to α-MnO2, γ-MnO2 and δ-MnO2. [Figure not available: see fulltext.]

Resolution of (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid using (1R,2R)-trans-cyclohexane-1,2-diamine

A simple and efficient method has been developed to resolve (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid [(±)-BINOL-3,3′-dicarboxylic acid] (±)-1 using inexpensive and readily accessible chiral resolving agent (1R,2R)-trans-cyclohexane-1,2-diamine 2. Enantiomers of BINOL-3,3′-dicarboxylic acid were obtained in good yields and enantiomeric purity, for example, (S)-(-)-1 was isolated in 34% yield with >99% ee and (R)-(+)-1 was obtained in 36% yield with >99% ee. The formation of diastereomeric salt A between (S)-BINOL-3,3′-dicarboxylic acid and (1R,2R)-trans-cyclohexane-1,2-diamine was ascertained by using IR, single crystal X-ray crystallography, and HRMS.