1334137-82-4

Basic information

• Product Name: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester
• Synonyms: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester;6-(4-Methoxyphenyl)-2-naphthoic Acid Ethyl Ester;Ethyl 6-(4-Methoxyphenyl)-2-naphthalenecarboxylate
• CAS NO: 1334137-82-4
• Molecular Formula: C₂₀H₁₈O₃
• Molecular Weight: 306.35512
• Mol File: 1334137-82-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 458.8±33.0 °C(Predicted)
• Appearance: /
• Density: 1.146±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester(1334137-82-4)
• EPA Substance Registry System: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester(1334137-82-4)

Safety Data

• Hazardous Substances Data: 1334137-82-4(Hazardous Substances Data)

Usage

Description

6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester is an organic compound that serves as an intermediate in the synthesis of Adapalene metabolites. It is characterized by its unique molecular structure, which includes a naphthalene ring, a 4-methoxyphenyl group, and an ethyl ester functional group.
Used in Pharmaceutical Industry:
6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester is used as a key intermediate in the synthesis of Adapalene (A225000) metabolites for the development of pharmaceutical products. Adapalene is a retinoid medication used to treat acne and other skin conditions, and this intermediate plays a crucial role in the production process, ensuring the efficacy and quality of the final product.

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 86471-14-9 ethyl 6-bromo-naphthalene-2-carboxylate 
• 33626-98-1 methyl 6-bromo-2-naphthoate 
• 5773-80-8 6-bromo-2-naphthoic acid 
• 132292-17-2 6-(4-methoxyphenyl)-2-naphthoic acid 
• 64-17-5 ethanol 

Downstream Products

• 106685-40-9 adapalene 
• 132292-17-2 6-(4-methoxyphenyl)-2-naphthoic acid 
• 1334138-60-1 C₅₀H₅₆N₄O₁₀S₂ 
• 1334136-11-6 (11aS)-7-methoxy-8-(3-(2-methoxy-5-(4-(6-(4-methoxyphenyl)-2-naphthoyl)piperazine-1-carbonyl)phenoxy)propoxy)-2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(11aH)-one 
• 1334137-61-9 C₁₈H₁₃ClO₂ 
• 1334137-43-7 C₃₀H₂₈N₂O₅ 
• 1334136-34-3 C₃₃H₃₃BrN₂O₅ 

Relevant articles and documents

New synthesis of 6[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid and evaluation of the influence of adamantyl group on the DNA binding of a naphthoic retinoid

6[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid (Adapalene), a synthetic aromatic retinoid specific for RARβ and RARγ receptors, has been prepared utilizing a Pd/C-mediated Suzuki coupling between 6-bromo-2-naphthoic acid and 4-methoxyphenyl boronic acid, followed by introduction of an adamantyl group in the position 3 of the formed 6-(4-methoxyphenyl)-2-naphthoic acid. The interaction of 6-(4-methoxyphenyl)-2- naphthoic acid/ethyl ester and the 3-adamantyl analogs with DNA was studied in aqueous solution at physiological conditions by UV-vis spectroscopy. The calculated binding constants Kligand-DNA ranged between 1.1 × 104 M-1 and 1.1 × 105 M-1, the higher values corresponding to those of the adamantylated compounds. Molecular modeling studies have emphasized that the intercalative binding of adapalene and its derivatives to DNA is mainly stabilized by hydrophobic interactions related to the presence of the adamantyl group.