Cas no 894802-19-8 (6-(2-Methoxyethoxy)nicotinaldehyde)

6-(2-Methoxyethoxy)nicotinaldehyde is a versatile nicotinaldehyde derivative featuring a 2-methoxyethoxy substituent at the 6-position of the pyridine ring. This compound is particularly valuable in organic synthesis as a key intermediate for constructing complex heterocyclic systems, pharmaceuticals, and functional materials. The methoxyethoxy side chain enhances solubility in polar organic solvents, facilitating its use in various reaction conditions. Its aldehyde group offers reactivity for condensation, nucleophilic addition, and other transformations, making it useful in the synthesis of Schiff bases, ligands, and biologically active molecules. The compound’s well-defined structure and functional group compatibility make it a reliable building block for medicinal chemistry and material science applications.
6-(2-Methoxyethoxy)nicotinaldehyde structure
894802-19-8 structure
Product Name:6-(2-Methoxyethoxy)nicotinaldehyde
CAS No:894802-19-8
MF:C9H11NO3
MW:181.188542604446
MDL:MFCD14582876
CID:2115149
PubChem ID:15067097
Update Time:2025-08-05

6-(2-Methoxyethoxy)nicotinaldehyde Chemical and Physical Properties

Names and Identifiers

    • 6-(2-methoxyethoxy)pyridine-3-carbaldehyde
    • JREMGXPAQPMEHI-UHFFFAOYSA-N
    • 6-(2-methoxyethoxy)nicotinaldehyde
    • 6-(2-Methoxyethoxy)nicotinaldehyde
    • MDL: MFCD14582876
    • Inchi: 1S/C9H11NO3/c1-12-4-5-13-9-3-2-8(7-11)6-10-9/h2-3,6-7H,4-5H2,1H3
    • InChI Key: JREMGXPAQPMEHI-UHFFFAOYSA-N
    • SMILES: O(C1C=CC(C=O)=CN=1)CCOC

Computed Properties

  • Exact Mass: 181.07389321g/mol
  • Monoisotopic Mass: 181.07389321g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 5
  • Complexity: 152
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 48.4
  • XLogP3: 0.5

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Additional information on 6-(2-Methoxyethoxy)nicotinaldehyde

Introduction to 6-(2-Methoxyethoxy)nicotinaldehyde (CAS No. 894802-19-8)

6-(2-Methoxyethoxy)nicotinaldehyde, identified by the Chemical Abstracts Service Number (CAS No.) 894802-19-8, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and bioorganic synthesis. This compound belongs to the aldehyde class, characterized by its functional group at the end of an aliphatic carbon chain, and it incorporates an ethoxy moiety linked to a methoxy group, further modifying its reactivity and potential biological activity. The structural features of 6-(2-Methoxyethoxy)nicotinaldehyde make it a versatile intermediate in the synthesis of more complex molecules, particularly in the development of novel therapeutic agents.

The nicotinaldehyde core of this compound is derived from nicotinic acid (niacin), a well-known B vitamin with established roles in energy metabolism and neurology. The introduction of an ethoxy group at the 6-position and a methoxy group on the ethyl chain introduces additional layers of functionality that can influence both the physical properties and the biological interactions of the molecule. This structural design allows for selective modifications, enabling chemists to explore a wide range of derivatives with tailored properties.

In recent years, there has been growing interest in aldehydes as key building blocks in medicinal chemistry due to their reactivity in condensation reactions, such as Schiff base formation, and their ability to serve as precursors for more complex heterocyclic structures. The aldehyde group in 6-(2-Methoxyethoxy)nicotinaldehyde is particularly valuable for these transformations, providing a site for nucleophilic addition reactions that can be harnessed to create diverse pharmacophores.

One of the most compelling aspects of 6-(2-Methoxyethoxy)nicotinaldehyde is its potential application in the synthesis of bioactive molecules. The combination of the nicotinamide scaffold with ethylene glycol-derived side chains offers a unique chemical profile that may be exploited in drug discovery. For instance, derivatives of this compound have shown promise in preclinical studies as modulators of enzymatic pathways involved in inflammation and oxidative stress. These pathways are implicated in a variety of diseases, including neurodegenerative disorders and cardiovascular conditions.

Recent advancements in computational chemistry have enabled more efficient screening of compounds like 6-(2-Methoxyethoxy)nicotinaldehyde for biological activity. Molecular docking simulations and virtual screening techniques allow researchers to predict how this molecule might interact with target proteins, providing insights into its potential therapeutic utility before costly experimental validation is undertaken. Such computational approaches are increasingly integral to modern drug discovery pipelines, streamlining the process from hit identification to lead optimization.

The synthesis of 6-(2-Methoxyethoxy)nicotinaldehyde itself presents an interesting challenge due to the need for precise functional group control. Traditional synthetic routes often involve multi-step processes that require careful optimization to achieve high yields and purity. However, recent methodologies have focused on greener and more efficient synthetic strategies, leveraging catalytic systems that minimize waste and energy consumption. These innovations align with broader trends in sustainable chemistry, where environmental impact is increasingly considered alongside traditional metrics of efficiency.

From a biochemical perspective, the methoxy and ethoxy substituents in 6-(2-Methoxyethoxy)nicotinaldehyde can influence its solubility and metabolic stability. The presence of these polar groups enhances water solubility compared to simpler aldehydes like benzaldehyde or formaldehyde, which may be advantageous for formulation into drug products. Additionally, metabolic studies suggest that such compounds are often metabolized via oxidation or reduction pathways mediated by cytochrome P450 enzymes, providing insights into potential drug-drug interactions.

The pharmaceutical industry has long been interested in nicotinamide derivatives due to their well-documented biological activities. Nicotinamide itself is known for its role as a cofactor in enzymatic reactions and its antioxidant properties. By modifying this scaffold with groups like (2-Methoxyethoxy), chemists aim to enhance or alter these properties for therapeutic benefit. For example, certain derivatives have demonstrated anti-inflammatory effects by inhibiting key enzymes such as lipoxygenases or cyclooxygenases.

In academic research circles, 6-(2-Methoxyethoxy)nicotinaldehyde has been employed as a starting material for exploring novel heterocyclic systems. Its reactivity allows for facile construction of fused rings or expanded aromatic structures through cyclization reactions. These heterocycles are often investigated for their potential as kinase inhibitors or other enzyme-targeting agents. The flexibility provided by the ethylene glycol side chain enables access to a diverse library of compounds with varying electronic distributions and steric profiles.

The development of new analytical techniques has also contributed to our understanding of 6-(2-Methoxyethoxy)nicotinaldehyde and its derivatives. High-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR) spectroscopy, and X-ray crystallography provide detailed structural information essential for confirming synthetic success and characterizing novel compounds. These tools are indispensable for ensuring the identity and purity of molecules used in both research and industrial settings.

Looking ahead, future research on 6-(2-Methoxyethoxy)nicotinaldehyde may focus on expanding its applications beyond traditional small-molecule drug discovery. Its structural motifs could be incorporated into biologics or used as scaffolds for peptidomimetics—molecules designed to mimic peptide sequences while offering improved pharmacokinetic properties. Furthermore, advances in biocatalysis may enable more sustainable production methods through enzymatic transformations tailored specifically for this compound.

The interdisciplinary nature of modern chemical research ensures that compounds like 6-(2-Methoxyethoxy)nicotinaldehyde will continue to play a pivotal role across multiple domains—from fundamental mechanistic studies to translational medicine. As our understanding deepens regarding structure-activity relationships within this class of molecules, we can anticipate further innovations that will shape future therapeutic strategies.

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