4-Chloro-1-naphthol
[CAS# 604-44-4]

Identification

• Classification: Biochemical >> Biochemical reagent >> Biological dye
• Name: 4-Chloro-1-naphthol
• Synonyms: 1-Chloro-4-naphthol; 1-Hydroxy-4-chloronaphthalene; 1-Chloro-4-hydroxynaphthalene; 4-Chloro-alpha-naphthol; 4-chloro-1-naphthalenol; NSC 44345
• Molecular Formula: C₁₀H₇ClO
• Molecular Weight: 178.61
• CAS Registry Number: 604-44-4
• EC Number: 210-068-5
• SMILES: C1=CC=C2C(=C1)C(=CC=C2Cl)O

Properties

• Density: 1.3±0.1 g/mL, Calc.^*
• Melting point: 120 ºC (Expl.)
• Index of Refraction: 1.684, Calc.^*
• Boiling Point: 332.1±15.0 ºC (760 mmHg), Calc.^*
• Flash Point: 154.6±20.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

4-Chloro-1-naphthol is an organic compound with the chemical formula C10H7ClO, consisting of a naphthalene ring substituted with a chlorine atom at the fourth position and a hydroxyl group at the first position. It is primarily used as an intermediate in the synthesis of various chemicals, and its applications span across different industries, including pharmaceuticals and dyes.

The compound was first described in the early 20th century as part of a broader effort to synthesize and study chlorinated naphthalene derivatives. Its relatively simple structure and the presence of both a hydroxyl group and a chlorine atom make it useful in the preparation of other organic compounds. The chloro group provides potential for further functionalization, while the hydroxyl group allows for reactions such as esterification or the formation of salts.

In the pharmaceutical industry, 4-chloro-1-naphthol has been studied for its potential role in the synthesis of various bioactive compounds. It is also employed as a reagent in the detection of certain metals, acting as a complexing agent due to its phenolic nature. The compound has found use as an analytical tool in chemistry, particularly for the detection of copper and other metals in aqueous solutions.

In the field of dyes and pigments, 4-chloro-1-naphthol serves as a precursor to other colored compounds, where the naphthalene structure imparts stability and color intensity. Its role in the synthesis of azo dyes, which are widely used in textiles and other products, highlights its industrial relevance.

4-Chloro-1-naphthol has also been explored for its potential antimicrobial and antifungal properties. Some studies have suggested that it may exhibit activity against certain microorganisms, although further research is needed to better understand its effectiveness in this area. As such, it has been considered for use in various biocidal applications.

Overall, 4-chloro-1-naphthol is a well-established compound with a variety of industrial and analytical applications. While its primary uses are in the synthesis of other chemicals, it also has potential as a reagent and in biocidal applications.

References

2023. An Antibody Ordered Assembly Functional BPE-ECL Platform for Aflatoxin B1 Detection. Food Analytical Methods, 16(12).
DOI: 10.1007/s12161-023-02558-6

2012. In Vitro Gastric and Intestinal Digestions of Pulsed Light-Treated Shrimp Extracts. Applied Biochemistry and Biotechnology, 166(2).
DOI: 10.1007/s12010-011-9534-2

1987. Improvement of light sensitive staining of immunoblots for routine analysis. Pathologie-biologie, 35(7).
URL: https://pubmed.ncbi.nlm.nih.gov/2444920