Chemical Properties
Off-white to beige powder
Uses
1-Naphthoic acid is used as an intermediate for the synthesis of pharmaceuticals, photochemicals, plant growth hormones, dyes and other organic compounds.
Definition
ChEBI: 1-naphthoic acid is a naphthoic acid carrying a carboxy group at position 1. It has a role as a fungal xenobiotic metabolite and a bacterial xenobiotic metabolite. It is a conjugate acid of a 1-naphthoate.
Application
1-Naphthoic acid has been used as a novel asymmetric chromophore for exciton-coupled circular dichroism (ECCD), which can be used to induce chirality
[1]. 1-Naphthoic acid has also been used as an organic synthesis reactant for the preparation of naphthanones, isocoumarin derivatives, and naphthalene carboxylic acid cellulose. Microcrystalline cellulose (MCC) and cellulose nanofibres (CNFs) were modified by esterification using 1-Naphthoic acid in a toluenesulfonyl chloride/pyridine solvent system to produce fluorophore labelled cellulose. Cellulose modification decreases the degradation temperature and hence the thermal stability of cellulose. After induction of naphthoate side chains, a glass transition temperature (Tg) of about 160 °C was observed. Cellulose naphthalenecarboxylate shows a strong ultraviolet (UV) absorption peak at 282 nm and has good fluorescent properties. Therefore, it can be used for fluorescent coatings, sensors and packaging
[2].
Purification Methods
Crystallise the acid from toluene (3mL/g) (charcoal), pet ether (b 80-100o), or aqueous 50% EtOH. The amide has m 202o (from EtOH). [Beilstein 9 IV 2402.]
References
[1] BIANCA SCHREDER. 1-Naphthoic acid: A new type of asymmetric chromophore for exciton-coupled circular dichroism (ECCD)[J]. Tetrahedron, asymmetry, 1996, 7 6: Pages 1543-1546. DOI:10.1016/0957-4166(96)00176-0.
[2] LEASE J, SAHIN Z M, FARID M A A, et al. Synthesis of Nanocellulose Derivatives through Esterification with Naphthoic Acid as a Fluorescent Additive[J]. ACS Sustainable Chemistry & Engineering, 2024, 343 1. DOI:10.1021/acssuschemeng.4c04206.
