2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde
[CAS# 1151539-21-7]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: 2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde
• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 243.26
• CAS Registry Number: 1151539-21-7
• SMILES: COC1=C(C=CC(=C1)OCC2=CC=CC=N2)C=O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.595, Calc.^*
• Boiling Point: 423.5±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 209.9±25.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P302+P352-P304+P340-P321-P330-P362+P364-P405-P501

Discovory and Applicatios

2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde is an organic compound that plays a significant role in medicinal chemistry and synthetic organic chemistry. Structurally, it is composed of a benzaldehyde core substituted with a methoxy group at the 2-position and a pyridin-2-ylmethoxy group at the 4-position. The presence of both aromatic and heterocyclic elements makes this compound versatile for use in drug design, particularly in the development of molecules with potential therapeutic applications.

The discovery of 2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde can be attributed to efforts in synthesizing benzaldehyde derivatives that incorporate heterocyclic groups. Such derivatives have been widely studied due to their ability to serve as intermediates in the synthesis of more complex bioactive molecules. The pyridine moiety, known for its basicity and ability to coordinate metal ions, is a key feature in many biologically active compounds, and its introduction into benzaldehyde derivatives enhances their chemical reactivity and biological potential.

In synthetic organic chemistry, 2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde has been employed as a building block in the preparation of various heterocyclic compounds. The aldehyde group at the benzaldehyde core provides a reactive site for condensation reactions, such as in the synthesis of Schiff bases or Mannich bases, both of which are important scaffolds in drug development. Schiff bases derived from this compound have shown promise in the development of metal-based drugs, as the pyridine group can chelate metal ions, forming complexes that exhibit antimicrobial, anticancer, or antioxidant properties.

This compound is also utilized in the synthesis of inhibitors targeting enzymes like protein kinases, which are crucial regulators of cellular signaling pathways. The combination of a methoxy group and a pyridinyl group within the same molecule provides the necessary balance of lipophilicity and hydrophilicity, which can enhance a molecule’s interaction with biological targets. Researchers have explored the potential of 2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde in the development of kinase inhibitors aimed at treating cancers and other proliferative diseases, where abnormal enzyme activity is a hallmark.

Beyond medicinal chemistry, 2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde finds applications in the preparation of advanced materials, particularly in coordination chemistry and supramolecular chemistry. The ability of the pyridine group to coordinate with transition metals makes this compound a valuable ligand in the construction of metal-organic frameworks (MOFs). These frameworks have garnered interest due to their applications in gas storage, catalysis, and as sensors. The aldehyde group of the compound can be functionalized to introduce additional reactive sites, further expanding the utility of this compound in creating multifunctional materials.

The synthetic utility of 2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde also extends to the field of asymmetric catalysis, where it has been used as a starting material in the preparation of chiral ligands. These ligands are crucial for facilitating enantioselective reactions, which are essential in producing single-enantiomer drugs. The electronic and steric properties of the methoxy and pyridinyl groups allow for fine-tuning of the reactivity and selectivity of these catalysts, thereby improving the efficiency of catalytic processes.

In summary, 2-Methoxy-4-(pyridin-2-ylmethoxy)benzaldehyde is an important chemical intermediate with diverse applications in both medicinal chemistry and materials science. Its ability to serve as a versatile building block in the synthesis of bioactive molecules, coordination compounds, and advanced materials has made it a valuable tool for researchers. As interest in heterocyclic compounds and metal-organic frameworks continues to grow, this compound is likely to see continued use in a range of innovative applications.