Production Method 1

3920-50-1

942319-16-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  16 h, rt

Reference

Diaminopyrazolo[1,5-a]pyrimidine-6-carbonitrile compounds as adenosine 2a receptor and adenosine 2b receptor antagonist and preparation thereof

, World Intellectual Property Organization, , ,

1-Ethyl-1H-pyrazole-3-carbaldehyde Raw materials

• 1H-pyrazole-3-carbaldehyde

1-Ethyl-1H-pyrazole-3-carbaldehyde Preparation Products

• 1-Ethyl-1H-pyrazole-3-carbaldehyde (942319-16-6)

• 1. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
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• 3. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
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• 4. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
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• 5. Distinction of trans–cis photoisomers with comparable optical properties in multiple-state photochromic systems – examining a molecule with three azobenzenes via in situ irradiation NMR spectroscopy?
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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aldehydes

Introduction to 1-Ethyl-1H-pyrazole-3-carbaldehyde (CAS No. 942319-16-6)

1-Ethyl-1H-pyrazole-3-carbaldehyde, identified by its CAS number 942319-16-6, is a significant compound in the realm of pharmaceutical and chemical research. This heterocyclic aldehyde derivative has garnered attention due to its versatile applications in synthetic chemistry and medicinal chemistry. The compound belongs to the pyrazole family, which is well-documented for its broad spectrum of biological activities and utility in drug development.

The structural motif of 1-Ethyl-1H-pyrazole-3-carbaldehyde consists of a pyrazole ring substituted with an ethyl group at the 1-position and a formyl group at the 3-position. This particular arrangement imparts unique reactivity, making it a valuable intermediate in the synthesis of more complex molecules. The formyl group, in particular, serves as a versatile handle for further functionalization, enabling the construction of intricate pharmacophores.

In recent years, there has been a surge in research focusing on pyrazole derivatives due to their demonstrated efficacy in various therapeutic areas. 1-Ethyl-1H-pyrazole-3-carbaldehyde has been explored as a key building block in the development of novel agrochemicals and pharmaceuticals. Its ability to undergo condensation reactions with amines and hydrazines, for instance, allows for the rapid assembly of pyrazolines and triazoles—heterocycles that are frequently encountered in bioactive molecules.

One of the most compelling aspects of 1-Ethyl-1H-pyrazole-3-carbaldehyde is its role in the synthesis of small-molecule inhibitors targeting enzyme-catalyzed processes. Enzymes such as kinases and oxidoreductases are integral to numerous cellular pathways, and their inhibition is often pivotal in treating diseases like cancer and inflammatory disorders. The aldehyde functionality in this compound provides an ideal site for covalent bond formation with nucleophilic residues on these enzymes, potentially leading to high-affinity inhibitors.

Recent studies have highlighted the compound's utility in generating libraries of diverse scaffolds for high-throughput screening (HTS). By leveraging its reactivity, researchers have been able to construct libraries enriched with unique structural motifs that may exhibit novel biological activities. This approach aligns with the growing trend toward fragment-based drug design, where small, potent molecules are combined to create more effective therapeutic agents.

The synthesis of 1-Ethyl-1H-pyrazole-3-carbaldehyde typically involves multi-step organic transformations starting from readily available precursors. Common synthetic routes include condensation reactions between ethyl acetoacetate and hydrazine hydrate to form ethyl 3-hydroxypyrazole-5-carboxylate, followed by dehydration to yield ethyl 5-hydroxypyrazolecarboxylate. Subsequent oxidation and reduction steps can then be employed to introduce the aldehyde functionality at the 3-position while preserving the ethyl group at the 1-position.

In terms of applications beyond drug discovery, 1-Ethyl-1H-pyrazole-3-carbaldehyde has found utility in materials science. Its ability to participate in cross-coupling reactions makes it a candidate for constructing polymers and functional materials with tailored properties. For instance, it can be used to generate polymers with specific electronic or optical characteristics by reacting with boronic acids or other coupling partners via Suzuki-Miyaura or Heck reactions.

The compound's stability under various reaction conditions also makes it an attractive choice for industrial applications. Unlike some reactive aldehydes that require stringent handling protocols, 1-Ethyl-1H-pyrazole-3-carbaldehyde can often be stored and handled under ambient conditions without significant degradation. This ease of handling reduces costs associated with storage and transportation while maintaining reactivity for downstream processes.

From a computational chemistry perspective, 1-Ethyl-1H-pyrazole-3-carbaldehyde has been subjected to extensive molecular modeling studies to elucidate its interactions with biological targets. Quantum mechanical calculations have provided insights into its electronic structure and reactivity, aiding researchers in designing more effective derivatives. These computational approaches are increasingly integral to modern drug discovery pipelines, complementing experimental techniques by predicting binding affinities and metabolic stability.

The future prospects for 1-Ethyl-1H-pyrazole-3-carbaldehyde are promising, given its versatility as a synthetic intermediate. As research continues to uncover new biological activities associated with pyrazole derivatives, demand for this compound is likely to grow. Its role in generating novel scaffolds for drug development positions it as a cornerstone molecule in medicinal chemistry libraries.

In conclusion, 1-Ethyl-1H-pyrazole-3-carbaldehyde (CAS No. 942319-16-6) is a multifaceted compound with broad applications across pharmaceuticals, agrochemicals, and materials science. Its unique structural features and reactivity make it an indispensable tool for synthetic chemists seeking to develop innovative molecular architectures. As research progresses，this compound will undoubtedly continue to play a pivotal role in advancing chemical biology and drug discovery efforts worldwide.

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