Cas no 1447914-90-0 (ethyl 4-formyl-1,3-thiazole-2-carboxylate)

Ethyl 4-formyl-1,3-thiazole-2-carboxylate is a versatile heterocyclic compound featuring both an aldehyde and an ester functional group on a thiazole core. This structure makes it a valuable intermediate in organic synthesis, particularly for constructing pharmacologically active molecules or functional materials. The formyl group at the 4-position allows for further derivatization via condensation or nucleophilic addition reactions, while the ester moiety at the 2-position offers flexibility for hydrolysis or transesterification. Its thiazole scaffold is significant in medicinal chemistry due to its prevalence in bioactive compounds. The compound’s reactivity and structural features make it suitable for applications in drug discovery, agrochemicals, and material science.
ethyl 4-formyl-1,3-thiazole-2-carboxylate structure
1447914-90-0 structure
Product Name:ethyl 4-formyl-1,3-thiazole-2-carboxylate
CAS No:1447914-90-0
MF:C7H7NO3S
MW:185.200380563736
CID:4600427
PubChem ID:117762896
Update Time:2025-05-24

ethyl 4-formyl-1,3-thiazole-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 2-Thiazolecarboxylic acid, 4-formyl-, ethyl ester
    • Ethyl 4-formylthiazole-2-carboxylate
    • ethyl 4-formyl-1,3-thiazole-2-carboxylate
    • Inchi: 1S/C7H7NO3S/c1-2-11-7(10)6-8-5(3-9)4-12-6/h3-4H,2H2,1H3
    • InChI Key: PSGICZLOVQODMF-UHFFFAOYSA-N
    • SMILES: S1C=C(C=O)N=C1C(OCC)=O

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Additional information on ethyl 4-formyl-1,3-thiazole-2-carboxylate

Ethyl 4-formyl-1,3-thiazole-2-carboxylate: A Comprehensive Overview

Ethyl 4-formyl-1,3-thiazole-2-carboxylate (CAS No. 1447914-90-0) is a compound of significant interest in the fields of organic chemistry and materials science. This compound belongs to the class of thiazole derivatives, which have been extensively studied due to their unique chemical properties and potential applications in drug discovery and material synthesis.

The structure of ethyl 4-formyl-1,3-thiazole-2-carboxylate consists of a thiazole ring system with a formyl group at position 4 and an ethoxycarbonyl group at position 2. The thiazole ring, a five-membered heterocyclic compound containing sulfur and nitrogen atoms, is known for its stability and reactivity in various chemical reactions. The presence of the formyl group introduces additional functionality, making this compound versatile for further modifications.

Recent studies have highlighted the potential of ethyl 4-formyl-1,3-thiazole-2-carboxylate in the development of new pharmaceutical agents. Researchers have explored its ability to act as a precursor for the synthesis of bioactive molecules with potential anti-inflammatory, anti-cancer, and antimicrobial properties. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibited significant inhibitory activity against certain enzymes involved in inflammatory pathways.

In addition to its pharmaceutical applications, ethyl 4-formyl-1,3-thiazole-2-carboxylate has shown promise in materials science. Its unique electronic properties make it a candidate for use in organic electronics, particularly in the development of semiconducting materials for flexible electronics and optoelectronic devices. A research team at the University of California reported that incorporating this compound into polymer blends significantly improved the charge transport properties of the resulting materials.

The synthesis of ethyl 4-formyl-1,3-thiazole-2-carboxylate involves a multi-step process that typically begins with the preparation of the thiazole ring followed by functionalization with the formyl and ethoxycarbonyl groups. Recent advancements in catalytic methods have enabled more efficient and environmentally friendly syntheses of this compound. For example, the use of palladium-catalyzed cross-coupling reactions has been reported to enhance both yield and purity in its production.

From an analytical standpoint, ethyl 4-formyl-1,3-thiazole-2-carboxylate has been characterized using various spectroscopic techniques such as NMR (Nuclear Magnetic Resonance), IR (Infrared Spectroscopy), and UV-vis spectroscopy. These analyses have provided insights into its molecular structure and electronic transitions, which are critical for understanding its reactivity and potential applications.

In conclusion, ethyl 4-form

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