Quinaldine
[CAS# 91-63-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Ethylpyridine
• Name: Quinaldine
• Synonyms: 2-Methylquinoline
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.19
• CAS Registry Number: 91-63-4
• EC Number: 202-085-1
• SMILES: CC1=NC2=CC=CC=C2C=C1

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*, 1.058 g/mL (Expl.)
• Melting point: -9 - -3 °C (decomp.) (Expl.)
• Index of Refraction: 1.625, Calc.^*, 1.612 (Expl.)
• Boiling Point: 246.5 °C (760 mmHg), Calc.^*, 258.4-261.1 °C (decomp.) (Expl.)
• Flash Point: 79.4 °C, Calc.^*, 79 °C (decomp.) (Expl.)

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

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302+H312-H302-H312-H315-H319-H341-H412
• Safety Statements: P203-P264-P264+P265-P270-P273-P280-P301+P317-P302+P352-P305+P351+P338-P317-P318-P321-P330-P332+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Germ cell mutagenicity	Muta.	2	H341

Discovery and Applications

Quinaldine, also known as 2-methylquinoline, is an organic compound with the chemical formula C9H11N. It is a derivative of quinoline, which consists of a benzene ring fused to a pyridine ring. Quinaldine was first synthesized in the 19th century and has since found a variety of applications in both industry and research.

Quinaldine is primarily used as a solvent and an intermediate in the synthesis of other chemicals. It is also used in the production of certain dyes and as a precursor to the synthesis of various pharmaceuticals. The compound is also found in some biological systems as a metabolite of certain alkaloids.

In industrial applications, quinaldine has been employed as a raw material in the production of various chemicals, particularly in the synthesis of alkaloid derivatives. One of its primary uses is as a precursor to quinaldine salts, which are employed in the synthesis of certain types of dyes and pigments. The compound’s chemical structure, which includes a nitrogen-containing heterocyclic ring, makes it useful for such applications.

Another important use of quinaldine is in the production of pharmaceuticals. It has been used in the synthesis of several compounds with biological activity, including antimalarial agents. Its role in drug development is linked to its ability to interact with certain enzymes and receptors in the body, making it a valuable building block for pharmaceutical chemistry.

In addition to its industrial and pharmaceutical uses, quinaldine has been studied for its potential in other areas of chemical research. It has been investigated for its reactivity and potential applications in chemical reactions, particularly in organic synthesis. The compound’s ability to undergo various types of substitution reactions makes it useful in the preparation of more complex organic molecules.

While quinaldine has a variety of applications, its toxicity has also been studied. It is considered to be harmful if inhaled, ingested, or absorbed through the skin, and its handling requires appropriate precautions. As a result, quinaldine is often used in controlled environments where proper safety measures are in place to prevent exposure.

In summary, quinaldine is an important chemical compound with a wide range of applications in industry, research, and pharmaceutical development. Its role as a precursor in the synthesis of various chemicals and as an intermediate in pharmaceutical production highlights its versatility. Further research into its properties and applications continues to expand our understanding of this valuable compound.

References

1979. Toxicity and teratogenicity of aromatic amines to Xenopus laevis. Bulletin of Environmental Contamination and Toxicology, 22(1-2).
DOI: 10.1007/bf02026923

2010. Amino Acyl Conjugates of Nitrogen Heterocycles as Potential Pharmacophores. The Journal of Organic Chemistry, 75(10).
DOI: 10.1021/jo100625y

2024. Synthesis and Luminescence Properties of (Z)-2-(Difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one, a New Unsymmetrical BODIPY Analogue. Russian Journal of Organic Chemistry, 60(4).
DOI: 10.1134/s1070428024040110