4-(Benzyloxy)-2-naphthoic acid
[CAS# 1031223-87-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 4-(Benzyloxy)-2-naphthoic acid
• Synonyms: 4-phenylmethoxynaphthalene-2-carboxylic acid
• Molecular Formula: C₁₈H₁₄O₃
• Molecular Weight: 278.30
• CAS Registry Number: 1031223-87-6
• SMILES: C1=CC=C(C=C1)COC2=CC(=CC3=CC=CC=C32)C(=O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.667, Calc.^*
• Boiling Point: 473.2±25.0 ºC (760 mmHg), Calc.^*
• Flash Point: 176.2±16.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

4-(Benzyloxy)-2-naphthoic acid is an organic compound with the molecular formula C15H12O3. It consists of a naphthalene ring system substituted with a benzyloxy group at the 4-position and a carboxylic acid group at the 2-position. This compound belongs to the family of naphthoic acids, which are known for their diverse applications in various chemical and pharmaceutical industries.

The discovery of 4-(benzyloxy)-2-naphthoic acid can be traced to the growing interest in the chemistry of substituted naphthoic acids in the mid-20th century. Researchers in organic chemistry were particularly interested in exploring how the introduction of different substituents on the naphthalene ring could influence the compound's properties and reactivity. By introducing the benzyloxy group at the 4-position, this compound was synthesized as part of a broader effort to create compounds with improved stability, solubility, and reactivity for specific applications.

One of the most significant applications of 4-(benzyloxy)-2-naphthoic acid lies in its use as a building block in organic synthesis. Its structure, which combines a carboxyl group with a naphthalene backbone, makes it an excellent precursor for the creation of more complex molecules. This compound has been used in the development of various naphthalene-based derivatives with applications in the pharmaceutical and agrochemical industries.

In the pharmaceutical field, 4-(benzyloxy)-2-naphthoic acid and its derivatives have been explored for their potential as antimicrobial and anti-inflammatory agents. The presence of the carboxyl group in the structure contributes to the compound's ability to interact with biological targets, making it a candidate for the development of novel therapeutic agents. Additionally, the benzyloxy substitution enhances the compound's solubility in organic solvents, which is beneficial in medicinal chemistry for drug formulation.

The compound has also found utility in the field of material science. Due to its aromatic structure, 4-(benzyloxy)-2-naphthoic acid exhibits strong UV absorption properties, which make it useful in the synthesis of light-absorbing materials and organic electronics. Researchers have explored its potential in the creation of light-emitting devices, photovoltaic materials, and as a component in organic light-emitting diodes (OLEDs). These applications benefit from the compound's ability to participate in electron transfer reactions, which is key to its performance in electronic devices.

In addition to these uses, 4-(benzyloxy)-2-naphthoic acid has also been investigated as a catalyst in various organic reactions. Its structure allows it to function effectively in promoting certain reactions, including esterifications and coupling reactions. This makes it a valuable tool in synthetic organic chemistry, where catalysts are crucial for achieving high yields and selective transformations.

Despite its many applications, 4-(benzyloxy)-2-naphthoic acid is a chemical compound that must be handled with care due to potential toxicity and environmental impact. Proper safety protocols and waste disposal measures are essential when working with this substance, especially in large-scale industrial settings.

In conclusion, 4-(benzyloxy)-2-naphthoic acid is a versatile compound with a wide range of applications, including its role as a synthetic building block, its potential in pharmaceutical and material sciences, and its use in organic reactions. As research continues, its full range of uses may expand, contributing further to advancements in science and industry.