Production Method 1

93-04-9

883-62-5

Reaction Conditions

1.1 Reagents: Butyllithium ,  Potassium tert-butoxide Solvents: Tetrahydrofuran ,  Hexane ;  5 min, -75 °C; 45 min, -75 °C
1.2 -75 °C → 25 °C

Reference

Metalation of 2-heterosubstituted naphthalenes at the 1- or 3- position: factors that may determine the regiochemistry

Ruzziconi, Renzo; et al, Synthesis, 2010, (9), 1531-1535

Production Method 2

92-70-6

883-62-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 30 min, 0 °C
1.2 10 h, rt
1.3 Reagents: Water ;  rt
2.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  rt → 130 °C; 6 h, 130 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 0 °C

Reference

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

Zhao, Xiao-Jing; et al, Angewandte Chemie, 2021, 60(13), 7061-7065

Production Method 3

3401-47-6

883-62-5

947-62-6

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  -78 °C
1.2 Reagents: sec-Butyllithium Solvents: Cyclohexane ;  1.25 h, -78 °C; 2 h, -78 °C → 30 °C
1.3 5 min, -30 °C

Reference

Synthesis of chiral binaphthyl derivatives

Wilson, Janet M., 1981, , ,

Production Method 4

93-04-9

883-62-5

947-62-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether

Reference

Heteroatom-facilitated lithiations

Gschwend, Heinz W.; Rodriguez, Herman R., Organic Reactions (Hoboken, 1979, 26,

Production Method 5

93-04-9

883-62-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  -78 °C
1.2 Reagents: sec-Butyllithium Solvents: Cyclohexane ;  10 min, -78 °C; 45 min, -78 °C; 10 min, -78 °C → -42 °C
1.3 -

Reference

Synthesis of chiral binaphthyl derivatives

Wilson, Janet M., 1981, , ,

Production Method 6

92-70-6

883-62-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt; 4 d, 50 °C
2.1 Reagents: Sodium hydroxide Solvents: Water ;  90 min, 100 °C; 100 °C → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  neutralized

Reference

Synthesis and structural analysis of oligo(naphthalene-2,3-diyl)s

Motomura, Takahisa; et al, Bulletin of the Chemical Society of Japan, 2005, 78(1), 142-146

Production Method 7

92-70-6

883-62-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Alumina ;  7 min, heated; cooled

Reference

Solid state S-methylation of thiols and O-methylation of phenols and naphthols with dimethyl sulfate under microwave irradiation

Heravi, Majid M.; et al, Phosphorus, 2005, 180(7), 1701-1712

Production Method 8

92-70-6

883-62-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  20 h, reflux
1.2 Reagents: Ammonium hydroxide Solvents: Water
2.1 -

Reference

Synthesis of chiral binaphthyl derivatives

Wilson, Janet M., 1981, , ,

Production Method 9

598-30-1

93-04-9

883-62-5

Reaction Conditions

1.1 Catalysts: Carbon dioxide

Reference

Studies in stereochemistry. 47. Asymmetric induction by leaving group in nucleophilic aromatic substitution

Wilson, Janet M.; et al, Journal of Organic Chemistry, 1984, 49(25), 4930-43

3-methoxynaphthalene-2-carboxylic acid Raw materials

• 3-Hydroxy-2-naphthoic acid
• lithium(1+) ion butan-2-ide
• 1-Bromo-2-methoxy-naphthalene
• 2-Methoxynaphthalene

3-methoxynaphthalene-2-carboxylic acid Preparation Products

• 2-Methoxy-1-naphthoic acid (947-62-6)
• 3-methoxynaphthalene-2-carboxylic acid (883-62-5)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenecarboxylic acids and derivatives Naphthalenecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

3-Methoxynaphthalene-2-Carboxylic Acid (CAS No. 883-62-5): A Comprehensive Overview

3-Methoxynaphthalene-2-carboxylic acid, a compound with the CAS registry number 883-62-5, is an organic aromatic compound that has garnered significant attention in various fields of chemistry and materials science. This compound is characterized by its unique structure, which combines a naphthalene ring system with a methoxy group and a carboxylic acid functional group. The combination of these functional groups imparts distinctive chemical and physical properties, making it a valuable material for research and industrial applications.

The naphthalene ring system in 3-methoxynaphthalene-2-carboxylic acid serves as the backbone of the molecule, providing stability and aromaticity. The methoxy group (-OCH?) attached at the 3-position introduces electron-donating effects, which can influence the electronic properties of the molecule. Meanwhile, the carboxylic acid group (-COOH) at the 2-position adds acidity and can participate in various chemical reactions, such as esterification or amidation. These functional groups make 3-methoxynaphthalene-2-carboxylic acid a versatile building block for synthesizing more complex molecules.

Recent studies have explored the potential of 3-methoxynaphthalene-2-carboxylic acid in advanced materials science. For instance, researchers have investigated its role in the development of organic semiconductors and light-emitting materials. The compound's ability to form stable crystalline structures and its favorable electronic properties make it a promising candidate for applications in optoelectronics. Additionally, its aromaticity and functional groups enable it to act as a precursor for synthesizing more complex aromatic compounds with tailored properties.

In terms of synthesis, 3-methoxynaphthalene-2-carboxylic acid can be prepared through various routes, including Friedel-Crafts acylation and subsequent oxidation or hydrolysis steps. Recent advancements in catalytic methods have improved the efficiency and selectivity of these reactions, leading to higher yields and purer products. The use of green chemistry principles in synthesis has also been explored, reducing the environmental impact of production processes.

The application of 3-methoxynaphthalene-2-carboxylic acid extends beyond materials science. It has been studied for its potential in pharmaceuticals, where its structure could serve as a scaffold for drug design. The compound's ability to interact with biological systems, particularly through its carboxylic acid group, makes it a candidate for bioactive molecules. Furthermore, its methoxy group can enhance solubility and bioavailability, which are critical factors in drug development.

Recent research has also focused on the environmental impact of 3-methoxynaphthalene-2-carboxylic acid. Studies have examined its biodegradability and toxicity under various conditions. Understanding these aspects is crucial for ensuring the safe use of the compound in industrial and pharmaceutical applications. Researchers have found that under specific environmental conditions, such as high pH or microbial activity, the compound can undergo degradation pathways that minimize its environmental footprint.

In conclusion, 3-methoxynaphthalene-2-carboxylic acid (CAS No. 883-62-5) is a multifaceted compound with significant potential across diverse fields. Its unique structure, functional groups, and chemical properties make it an invaluable material for both fundamental research and practical applications. As ongoing studies continue to uncover new insights into its properties and uses, this compound is poised to play an increasingly important role in advancing modern science and technology.

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