Production Method 1

31166-29-7

89281-29-8

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol

Reference

Herbicidal thienylureas. II

Stanetty, Peter; Puschautz, Erhard, Monatshefte fuer Chemie, 1987, 120(1), 65-72

Production Method 2

5380-42-7

89281-29-8

Reaction Conditions

1.1 Reagents: Chlorosuccinimide ,  Sulfuric acid Solvents: Trifluoroacetic acid ;  0 °C; 10 min, 0 °C

Reference

An efficient and facile process for synthesis of 4,5-dichlorothiophene-2-carboxylic acid using N-chlorosuccinimide

Wang, Peng; Ji, Min; Sha, Fei, Journal of Chemical Research, 2014, 38(10), 622-624

Production Method 3

17249-79-5

89281-29-8

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Silver carbonate ,  CataCXium A Solvents: Dimethylformamide ;  2 bar, rt → 90 °C; 15 h, 90 °C
1.2 Solvents: Dimethylformamide ;  2 h, 90 °C

Reference

Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives

Lee, Mijung; Hwang, Young Kyu ; Kwak, Jaesung, Organometallics, 2021, 40(18), 3136-3144

Methyl 4,5-dichlorothiophene-2-carboxylate Raw materials

• Methyl thiophene-2-carboxylate
• 2,3-Dichlorothiophene
• 4,5-Dichlorothiophene-2-carboxylic Acid

Methyl 4,5-dichlorothiophene-2-carboxylate Preparation Products

• Methyl 4,5-dichlorothiophene-2-carboxylate (89281-29-8)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Thiophenes Thiophene carboxylic acids and derivatives

Methyl 4,5-dichlorothiophene-2-carboxylate (CAS No. 89281-29-8): An Overview of Its Properties, Applications, and Recent Research

Methyl 4,5-dichlorothiophene-2-carboxylate (CAS No. 89281-29-8) is a versatile organic compound that has garnered significant attention in the fields of chemistry and pharmaceuticals due to its unique properties and potential applications. This compound belongs to the class of thiophenes, which are five-membered heterocyclic compounds containing a sulfur atom. The presence of chlorine atoms and the ester group in its structure imparts specific chemical and biological activities that make it a valuable intermediate in various synthetic processes.

The molecular formula of Methyl 4,5-dichlorothiophene-2-carboxylate is C₆H₃Cl₂O₂S, and its molecular weight is approximately 206.05 g/mol. The compound is a white to off-white crystalline solid at room temperature and is soluble in common organic solvents such as dichloromethane, acetone, and ethanol. Its stability under various conditions makes it suitable for use in a wide range of chemical reactions and processes.

In the context of pharmaceutical research, Methyl 4,5-dichlorothiophene-2-carboxylate has been explored for its potential as an intermediate in the synthesis of biologically active compounds. Recent studies have highlighted its role in the development of novel drugs targeting various diseases. For instance, a study published in the Journal of Medicinal Chemistry reported the use of this compound as a key intermediate in the synthesis of antiviral agents with potent activity against influenza viruses. The unique structural features of Methyl 4,5-dichlorothiophene-2-carboxylate allow for the introduction of functional groups that enhance the antiviral efficacy of the final products.

Beyond antiviral applications, Methyl 4,5-dichlorothiophene-2-carboxylate has also shown promise in the development of anticancer drugs. A research team from the University of California, Los Angeles (UCLA) demonstrated that derivatives of this compound exhibit selective cytotoxicity against cancer cells while sparing normal cells. The mechanism of action involves the disruption of cellular signaling pathways that are often dysregulated in cancer cells. This finding opens up new avenues for the design and synthesis of more effective anticancer agents.

In addition to its pharmaceutical applications, Methyl 4,5-dichlorothiophene-2-carboxylate has found utility in materials science and organic synthesis. Its thiophene core provides a stable platform for the construction of conjugated systems with interesting electronic properties. For example, researchers at the Massachusetts Institute of Technology (MIT) utilized this compound as a building block in the synthesis of conductive polymers for use in organic electronics. The resulting materials exhibited high electrical conductivity and excellent thermal stability, making them suitable for applications such as flexible displays and wearable devices.

The synthetic versatility of Methyl 4,5-dichlorothiophene-2-carboxylate is further evidenced by its use in the preparation of functionalized materials for catalysis and environmental remediation. A study published in Green Chemistry described a method for synthesizing metal-organic frameworks (MOFs) using this compound as a ligand. The resulting MOFs showed high efficiency in removing heavy metal ions from contaminated water, highlighting their potential for environmental applications.

In conclusion, Methyl 4,5-dichlorothiophene-2-carboxylate (CAS No. 89281-29-8) is a multifaceted compound with a wide range of applications in pharmaceuticals, materials science, and environmental remediation. Its unique chemical structure and synthetic versatility make it an invaluable intermediate in various research and industrial processes. Ongoing research continues to uncover new possibilities for its use, underscoring its importance in modern chemistry and related fields.

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