1-Naphthoic acid Chemical Properties

Melting point:

157-160 °C (lit.)

Boiling point:

300 °C (lit.)

Density 

1.398

refractive index 

1.4600 (estimate)

Flash point:

195°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Slightly soluble in hot water; freely soluble in hot ethanol, ether

form 

Powder

pka

3.7(at 25℃)

color 

Slightly yellow to brown

Specific Gravity

1.398

PH Range

Non& uorescence (2.5) to blue & uorescence (3.5)

Water Solubility 

Freely soluble in hot alcohol and ether. Slightly soluble in hot water.

λmax

293nm

Merck 

14,6381

BRN 

1908896

Stability:

Stable. Incompatible with strong bases, strong oxidizing agents.

Major Application

Photoresists, recording materials, waveguides, battery, ink, rubber, plastic films, agriculture, cosmetics, Sunscreen, method for preserving food, drugs, biosensors

InChIKey

LNETULKMXZVUST-UHFFFAOYSA-N

CAS DataBase Reference

86-55-5(CAS DataBase Reference)

NIST Chemistry Reference

1-Naphthalenecarboxylic acid(86-55-5)

EPA Substance Registry System

1-Naphthalenecarboxylic acid (86-55-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25-37

WGK Germany 

2

RTECS 

QL0960000

TSCA 

Yes

HS Code 

29163900

MSDS

• Language:English Provider:a-Naphthoic Acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-Naphthoic acid Usage And Synthesis

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].

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 425, 1943
Tetrahedron Letters, 22, p. 1013, 1981 DOI: 10.1016/S0040-4039(01)82853-7

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.

1-Naphthoic acid(86-55-5)Related Product Information

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