2-Methyl-1,4-dihydroquinolin-4-one
[CAS# 5660-24-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 2-Methyl-1,4-dihydroquinolin-4-one
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• CAS Registry Number: 5660-24-2
• EC Number: 210-140-6
• SMILES: CC1=CC(=O)C2=CC=CC=C2N1

Properties

• Solubility: 1849 mg/L (25 °C water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.574, Calc.^*
• Melting point: 88.13 °C
• Boiling Point: 270.8±40.0 °C (760 mmHg), Calc.^*, 296.90 °C
• Flash Point: 120.1±27.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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

Discovery and Applications

2-Methyl-1,4-dihydroquinolin-4-one is a noteworthy compound in the field of organic chemistry, particularly recognized for its diverse applications in medicinal chemistry and material science. This compound was first synthesized in the mid-20th century as researchers explored the properties of quinoline derivatives. The quest for novel heterocyclic compounds led to the development of 2-methyl-1,4-dihydroquinolin-4-one, which features a unique fused ring system that imparts significant chemical reactivity and biological activity.

The structure of 2-methyl-1,4-dihydroquinolin-4-one consists of a quinoline core with a methyl group at the second position and a saturated carbon-carbon bond adjacent to the nitrogen atom. This structural configuration is essential for its reactivity, allowing it to participate in various chemical reactions. Researchers have found that 2-methyl-1,4-dihydroquinolin-4-one can act as a versatile building block in organic synthesis, particularly in the creation of more complex molecular architectures.

One of the primary applications of 2-methyl-1,4-dihydroquinolin-4-one is in the field of medicinal chemistry. Studies have demonstrated that this compound exhibits significant biological activities, including anti-inflammatory, antimicrobial, and antioxidant properties. Its ability to inhibit specific enzymes and interact with biological targets makes it a valuable candidate for drug development. Researchers are exploring its potential as a scaffold for designing novel pharmaceuticals, particularly in the treatment of diseases such as cancer and infectious diseases.

In addition to its medicinal applications, 2-methyl-1,4-dihydroquinolin-4-one is utilized in material science. Its unique chemical properties allow it to be employed as a dye and pigment in various industrial applications. The compound's ability to absorb light and exhibit vivid colors makes it suitable for use in coatings, plastics, and other materials where color and stability are essential.

The versatility of 2-methyl-1,4-dihydroquinolin-4-one extends to its use in chemical research as well. It serves as an important intermediate in the synthesis of other biologically active compounds and functional materials. Researchers have also studied its role in various catalytic processes, contributing to the development of more efficient synthetic methodologies.

Safety and handling considerations are vital when working with 2-methyl-1,4-dihydroquinolin-4-one, as with any chemical compound. Proper laboratory practices and adherence to safety regulations are necessary to ensure the safe use of this compound in research and industrial applications.

In summary, 2-methyl-1,4-dihydroquinolin-4-one represents an important compound in organic chemistry, with significant implications for medicinal chemistry and material science. Its discovery opened avenues for further research into quinoline derivatives, enhancing our understanding of their chemical and biological properties. As scientists continue to investigate its potential, 2-methyl-1,4-dihydroquinolin-4-one is poised to contribute to advancements in drug development and material innovation.

References

2023. Topological analysis and reactivity study of monomeric and dimeric forms of 2-methyl-4(1H)-quinolone: a computational study. Journal of Molecular Modeling, 29(11).
DOI: 10.1007/s00894-023-05779-y

2010. Endochin Optimization: Structure-Activity and Structure-Property Relationship Studies of 3-Substituted 2-Methyl-4(1H)-quinolones with Antimalarial Activity. Journal of Medicinal Chemistry, 53(18).
DOI: 10.1021/jm1007903

2015. Synthesis, spectroscopic investigations and computational study of monomeric and dimeric structures of 2-methyl-4-quinolinol. Research on Chemical Intermediates, 41(12).
DOI: 10.1007/s11164-015-2084-4