6-Hydroxyquinoline-4-carboxylic acid
[CAS# 4312-44-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 6-Hydroxyquinoline-4-carboxylic acid
• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.17
• CAS Registry Number: 4312-44-1
• EC Number: 877-953-1
• SMILES: C1=CC2=NC=CC(=C2C=C1O)C(=O)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.730, Calc.^*
• Boiling Point: 426.7±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 211.9±23.2 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

6-Hydroxyquinoline-4-carboxylic acid is a heterocyclic organic compound that has garnered significant attention in scientific research due to its versatile chemical structure and wide range of applications. Its combination of a quinoline ring system, hydroxyl group, and carboxylic acid moiety makes it a valuable molecule in organic synthesis, materials science, and pharmaceutical development.

The compound was first identified during studies on quinoline derivatives, which have a rich history in medicinal chemistry and dye industries. Quinoline derivatives, including 6-hydroxyquinoline-4-carboxylic acid, have been synthesized through various chemical methods, with modern approaches focusing on efficiency and sustainability. One common synthetic route involves functionalizing the quinoline ring via hydroxylation and carboxylation reactions.

6-Hydroxyquinoline-4-carboxylic acid exhibits notable chemical properties, such as the ability to form metal complexes and participate in hydrogen bonding. These properties make it an important ligand in coordination chemistry. Its derivatives are widely used in the preparation of luminescent materials, catalysts, and chelating agents for metal ion detection.

In pharmaceutical research, 6-hydroxyquinoline-4-carboxylic acid serves as a scaffold for designing biologically active compounds. It has been explored for its antimicrobial, anticancer, and anti-inflammatory properties. The hydroxyl and carboxylic acid groups provide sites for further functionalization, enabling the synthesis of diverse molecules with potential therapeutic applications.

This compound is also used in material science, particularly in the development of organic semiconductors and light-emitting devices. Its ability to interact with transition metals has been leveraged to create metal-organic frameworks (MOFs) with applications in gas storage, separation, and catalysis.

Ongoing research focuses on expanding the applications of 6-hydroxyquinoline-4-carboxylic acid in sustainable technologies. Studies are investigating its role in solar cell development and as a precursor for bioactive polymers. Efforts to optimize its synthesis aim to reduce environmental impact while improving yield and purity.

References

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