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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzenesulfonic acids and derivatives Benzenesulfonate esters

Methyl 3-{(4-Methylphenyl)sulfonyloxy}-2-thiophenecarboxylate (CAS 181226-89-1): A Versatile Sulfonyloxy Thiophene Derivative in Modern Chemistry

Methyl 3-{(4-Methylphenyl)sulfonyloxy}-2-thiophenecarboxylate (CAS 181226-89-1) is a specialized sulfonyloxy thiophene derivative that has gained significant attention in pharmaceutical and material science research. This compound, featuring both thiophene carboxylate and tosyloxy functional groups, serves as a key intermediate in organic synthesis. Its molecular structure combines the electron-rich thiophene ring with the versatile reactivity of sulfonate esters, making it valuable for constructing complex molecular architectures.

The growing interest in heterocyclic compounds like Methyl 3-{(4-Methylphenyl)sulfonyloxy}-2-thiophenecarboxylate stems from their applications in drug discovery and functional materials. Researchers particularly value its potential as a building block for small molecule pharmaceuticals, where the thiophene moiety often contributes to biological activity. The compound's tosyloxy group serves as an excellent leaving group, enabling various nucleophilic substitution reactions that are fundamental in medicinal chemistry.

Recent advancements in catalytic cross-coupling reactions have highlighted the importance of thiophene-based intermediates like CAS 181226-89-1. The compound's stability under various reaction conditions makes it suitable for palladium-catalyzed couplings, a hot topic in current synthetic methodology research. Its application extends to the development of organic electronic materials, where thiophene derivatives are known for their excellent charge transport properties.

The synthesis of Methyl 3-{(4-Methylphenyl)sulfonyloxy}-2-thiophenecarboxylate typically involves the tosylation of thiophene carboxylic acids, followed by esterification. This process has been optimized in recent years to achieve higher yields and purity, addressing common questions about scale-up challenges in fine chemical production. The compound's crystalline nature and good solubility in common organic solvents contribute to its handling advantages in laboratory settings.

In pharmaceutical research, this sulfonyloxy thiophene derivative has shown promise as a precursor for kinase inhibitors and other therapeutic agents. The 4-methylphenylsulfonyl group enhances the compound's stability while maintaining reactivity, a balance that organic chemists frequently search for in building blocks. Its applications in creating biologically active thiophenes align with current trends in targeted drug development.

Material scientists have explored CAS 181226-89-1 for developing conjugated polymers with unique optoelectronic properties. The compound's ability to participate in polymerization reactions while preserving the thiophene backbone's electronic characteristics makes it valuable for organic electronics research. This connects to growing interest in sustainable materials and organic photovoltaics, frequently searched topics in green chemistry.

Quality control of Methyl 3-{(4-Methylphenyl)sulfonyloxy}-2-thiophenecarboxylate typically involves advanced analytical techniques like HPLC and NMR spectroscopy, addressing common questions about compound characterization in fine chemical synthesis. The availability of high-purity material has increased in response to demand from both academic and industrial researchers working on structure-activity relationship studies.

Recent publications have demonstrated innovative uses of this thiophene derivative in click chemistry applications and bioconjugation strategies. Its compatibility with various catalytic systems makes it a versatile tool for synthetic chemists developing new carbon-heteroatom bond formation methodologies. These applications align with current research trends toward more efficient and selective synthetic transformations.

The stability profile of CAS 181226-89-1 under different storage conditions is another frequently searched topic. Proper handling typically involves protection from moisture and storage at controlled temperatures, following standard practices for reactive esters. These practical considerations are important for researchers planning multi-step syntheses using this valuable intermediate.

As research into functionalized thiophenes continues to expand, Methyl 3-{(4-Methylphenyl)sulfonyloxy}-2-thiophenecarboxylate maintains its position as an important building block in both academic and industrial settings. Its combination of stability and reactivity, along with the growing importance of thiophene-based scaffolds in medicinal chemistry, ensures ongoing interest in this specialized compound.

• 89643-68-5(2,5-Thiophenedicarboxylic acid, 3-[[(4-bromophenyl)sulfonyl]oxy]-4-methyl-, 2,5-diethyl ester)
• 89629-71-0(2,5-Thiophenedicarboxylic acid, 3-[[(4-bromophenyl)sulfonyl]oxy]-4-methyl-, 2,5-dibutyl ester)
• 89629-70-9(2,5-Thiophenedicarboxylic acid,3-[[(4-bromophenyl)sulfonyl]oxy]-4-methyl-, bis(1-methylethyl) ester)
• 89629-69-6(2,5-Thiophenedicarboxylic acid, 3-[[(4-bromophenyl)sulfonyl]oxy]-4-methyl-, 2,5-dipropyl ester)
• 89629-75-4(2,5-Thiophenedicarboxylic acid, 3-methyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, 2,5-dipropyl ester)
• 89629-73-2(2,5-Thiophenedicarboxylic acid, 3-methyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, 2,5-dimethyl ester)
• 89629-78-7(2,5-Thiophenedicarboxylic acid, 3-methyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, 2,5-di-2-propen-1-yl ester)
• 89629-77-6(2,5-Thiophenedicarboxylic acid, 3-methyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, 2,5-dibutyl ester)
• 89629-74-3(2,5-Thiophenedicarboxylic acid, 3-methyl-4-[[(4-methylphenyl)sulfonyl]oxy]-, 2,5-diethyl ester)
• 89629-72-1(2,5-Thiophenedicarboxylic acid, 3-[[(4-bromophenyl)sulfonyl]oxy]-4-methyl-, 2,5-bis(2-methylpropyl) ester)