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Comprehensive Overview of 3-Ethynylisonicotinaldehyde (CAS No. 1196153-32-8): Properties, Applications, and Industry Insights

3-Ethynylisonicotinaldehyde (CAS No. 1196153-32-8) is a highly specialized organic compound that has garnered significant attention in pharmaceutical and materials science research. This aldehyde derivative features a unique combination of an ethynyl group and an isonicotinaldehyde scaffold, making it a versatile building block for click chemistry applications and heterocyclic synthesis. Its molecular structure, C₈H₅NO, offers reactive sites for cross-coupling reactions, a feature increasingly demanded in modern drug discovery pipelines.

Recent trends in AI-driven molecular design have highlighted compounds like 3-Ethynylisonicotinaldehyde as key intermediates for high-throughput screening. Researchers frequently search for "click chemistry reagents 2024" or "isonicotinaldehyde derivatives applications," reflecting growing interest in modular synthesis approaches. The compound's terminal alkyne functionality enables efficient Huisgen cycloaddition, a reaction mechanism widely adopted in bioconjugation and nanomaterial functionalization.

From a synthetic chemistry perspective, 1196153-32-8 demonstrates exceptional reactivity in Palladium-catalyzed transformations. Laboratories focusing on kinase inhibitor development often utilize this compound to construct pyridine-based pharmacophores, addressing popular search queries like "building blocks for kinase inhibitors." Its electron-deficient pyridine ring enhances compatibility with microwave-assisted synthesis techniques, a hot topic in green chemistry forums.

The compound's role extends to material science, where it serves as a precursor for conducting polymers and metal-organic frameworks (MOFs). Industry reports tracking "organic electronic materials 2024" frequently reference ethynyl-substituted aldehydes as critical components for optoelectronic devices. Its conjugated system allows for precise tuning of HOMO-LUMO gaps, a property extensively studied for organic photovoltaic applications.

Quality control of 3-Ethynylisonicotinaldehyde requires advanced analytical techniques. Chromatographic methods like HPLC-UV and LC-MS are commonly employed to verify purity, responding to frequent searches for "CAS 1196153-32-8 analysis methods." The compound typically appears as a white to pale yellow crystalline powder with characteristic FT-IR absorption at 1700-1720 cm^-1 (C=O stretch) and 2100-2120 cm^-1 (C≡C stretch).

Storage and handling recommendations for 1196153-32-8 emphasize protection from moisture and oxygen, with optimal preservation under argon atmosphere at -20°C. These protocols align with current industry standards for air-sensitive intermediates, a subject frequently explored in queries like "best practices for alkyne storage." The compound's thermal stability has been confirmed through differential scanning calorimetry (DSC) studies up to 150°C.

Emerging applications in biomedical imaging leverage the compound's ability to form fluorescent probes via CuAAC reactions. This connects to trending searches about "small molecule imaging agents" and "bioorthogonal chemistry." Recent patent literature describes its incorporation into PET tracer development, particularly for neurological target visualization.

Market analysts note increasing demand for 3-Ethynylisonicotinaldehyde in contract research organizations, driven by its utility in fragment-based drug design. The compound's molecular weight (131.13 g/mol) and logP (~1.2) make it particularly valuable for developing CNS-penetrant molecules, addressing persistent challenges in blood-brain barrier permeability optimization.

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