Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
[CAS# 161798-02-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
• Molecular Formula: C₁₄H₁₂N₂O₃S
• Molecular Weight: 288.32
• CAS Registry Number: 161798-02-3
• SMILES: CCOC(=O)C1=C(N=C(S1)C2=CC(=C(C=C2)O)C#N)C

Properties

• Density: 1.38

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate, also known as cyano-hydroxyphenyl methylthiazole carboxylate, was synthesized through organic chemistry research aimed at exploring the reactivity and potential applications of thiazole derivatives. The discovery of this compound can be traced back to investigations into the functionalization of thiazole rings with cyano and hydroxyphenyl groups. By reacting 3-cyano-4-hydroxybenzaldehyde with thioamide and ethyl chloroacetate, researchers successfully synthesized ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate. This compound's discovery opened avenues for further research into its chemical properties and potential applications in pharmaceuticals, materials science, and agrochemicals.

Thiazole carboxylates, including ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate, have demonstrated antibacterial properties against a wide range of bacterial strains. These compounds inhibit bacterial growth by interfering with essential cellular processes, such as DNA replication or protein synthesis, making them potential candidates for the development of antibacterial drugs. Thiazole derivatives possess anti-inflammatory properties due to their ability to modulate immune responses and reduce inflammation. Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate can inhibit the production of pro-inflammatory mediators, such as cytokines and prostaglandins, contributing to its potential therapeutic applications in inflammatory diseases.

Thiazole carboxylates exhibit interesting photophysical properties, including fluorescence and phosphorescence, making them useful in the synthesis of fluorescent materials and sensors. Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate and its derivatives can be incorporated into fluorescent dyes, polymers, or nanoparticles for various applications, such as chemical sensing, bioimaging, and optoelectronic devices. Thiazole-based compounds are utilized in the development of electrochemical sensors for detecting analytes, such as heavy metals, organic pollutants, or biological molecules. Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate can be immobilized on electrode surfaces to selectively capture target molecules and generate measurable electrical signals, enabling rapid and sensitive detection in environmental monitoring, healthcare, or food safety.

Thiazole carboxylates have herbicidal properties and are used in the development of agrochemicals for weed control in agriculture. Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate and its derivatives exhibit selective herbicidal activity against specific weed species, contributing to crop protection and yield enhancement. Some thiazole derivatives, including ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate, have been investigated for their potential as plant growth regulators (PGRs). These compounds modulate physiological processes in plants, such as seed germination, root development, and flowering, leading to improved crop productivity and stress tolerance.

Ongoing research focuses on exploring the pharmacological potential of ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate and its derivatives for the treatment of bacterial infections, inflammatory diseases, and other therapeutic indications. Rational drug design approaches aim to optimize the compound's pharmacokinetic properties and target selectivity through structure-activity relationship studies and computational modeling. In agriculture, efforts are underway to develop novel thiazole-based herbicides with improved efficacy, environmental safety, and resistance management properties. Research initiatives explore new synthetic routes, formulation technologies, and application methods to enhance the performance and sustainability of thiazole-derived agrochemicals.

References

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