Production Method 1

7311-70-8

89280-91-1

Reaction Conditions

1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Chloroform ;  0 °C; 0 °C → rt; 4 h, rt
1.2 Solvents: Chloroform ;  0 °C
1.3 Reagents: Pyridine ;  0 °C → rt; 24 h, rt

Reference

Wide Bandgap Polymer Donor with Acrylate Side Chains for Non-Fullerene Acceptor-Based Organic Solar Cells

Yuan, Yi; Kumar, Pankaj; Ngai, Jenner H. L.; Gao, Xiguang; Li, Xu; et al, Macromolecular Rapid Communications, 2022, 43(20),

Production Method 2

57248-40-5

89280-91-1

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  rt → 0 °C; 2 h, rt

Reference

Nickel-Catalyzed Suzuki Polycondensation for Controlled Synthesis of Ester-Functionalized Conjugated Polymers

Qiu, Yunyan; Worch, Joshua C.; Fortney, Andria; Gayathri, Chakicherla; Gil, Roberto R.; et al, Macromolecules (Washington, 2016, 49(13), 4757-4762

Production Method 3

57248-40-5

89280-91-1

Reaction Conditions

1.1 12 h, reflux

Reference

Hydrogen vs. halogen bonding in crystals of 2,5-dibromothiophene-3-carboxylic acid derivatives

Baykov, Sergey V. ; Semenov, Artem V.; Presnukhina, Sofia I.; Novikov, Alexander S.; Shetnev, Anton A.; et al, Journal of Molecular Structure, 2022, 1260,

Production Method 4

22913-26-4

89280-91-1

Reaction Conditions

1.1 Reagents: Bromine Solvents: Acetic acid ;  24 h, rt → 60 °C
1.2 Reagents: Sodium bisulfite ;  rt

Reference

Room Temperature Processed Highly Efficient Large-Area Polymer Solar Cells Achieved with Molecular Engineering of Copolymers

Rasool, Shafket; Vu, Doan Van; Song, Chang Eun; Lee, Hang Ken; Lee, Sang Kyu; et al, Advanced Energy Materials, 2019, 9(21),

Production Method 5

22913-26-4

89280-91-1

Reaction Conditions

1.1 Reagents: Bromine

Reference

Gold nanoparticle-templated assembly of oligothiophenes: preparation and film properties

Saitou, Ken-ichi; Nishiyabu, Ryuhei; Iyoda, Masahiko; Kubo, Yuji, Tetrahedron, 2011, 67(50), 9685-9689

Methyl 2,5-dibromothiophene-3-carboxylate Raw materials

• 2,5-Dibromothiophene-3-carboxylic acid
• 3-Thiophenecarbonyl chloride, 2,5-dibromo-
• methyl thiophene-3-carboxylate

Methyl 2,5-dibromothiophene-3-carboxylate Preparation Products

• Methyl 2,5-dibromothiophene-3-carboxylate (89280-91-1)

• 1. An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries
  Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon Song Phys. Chem. Chem. Phys., 2014,16, 5295-5300
• 2. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 3. An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode
  Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. Killard Analyst, 2008,133, 391-399
• 4. An intramolecular tryptophan-condensation approach for peptide stapling?
  Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392
• 5. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156

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

Comprehensive Overview of Methyl 2,5-dibromothiophene-3-carboxylate (CAS No. 89280-91-1)

Methyl 2,5-dibromothiophene-3-carboxylate (CAS No. 89280-91-1) is a highly versatile thiophene derivative widely utilized in organic synthesis, pharmaceuticals, and material science. This compound, characterized by its brominated thiophene core and ester functional group, has garnered significant attention due to its unique reactivity and applications in heterocyclic chemistry. Researchers and industries value its role as a building block for complex molecules, particularly in the development of functional materials and bioactive compounds.

The growing interest in sustainable chemistry and green synthesis has propelled the demand for efficient organic intermediates like Methyl 2,5-dibromothiophene-3-carboxylate. Its compatibility with cross-coupling reactions, such as Suzuki-Miyaura and Stille couplings, makes it indispensable for constructing π-conjugated systems used in organic electronics and optoelectronic devices. Recent studies highlight its potential in designing OLED materials and photovoltaic cells, aligning with the global shift toward renewable energy solutions.

In the pharmaceutical sector, Methyl 2,5-dibromothiophene-3-carboxylate serves as a precursor for drug discovery, particularly in synthesizing thiophene-based therapeutics. Its structural motif is prevalent in anticancer agents, antimicrobial compounds, and anti-inflammatory drugs. The compound’s regioselective bromination offers precise control over molecular modifications, a critical factor in medicinal chemistry optimization. This aligns with the rising focus on personalized medicine and targeted drug delivery systems.

From an industrial perspective, Methyl 2,5-dibromothiophene-3-carboxylate is pivotal in producing agrochemicals and specialty chemicals. Its derivatives are explored for crop protection formulations, addressing challenges in sustainable agriculture. The compound’s stability under diverse reaction conditions also makes it a candidate for high-throughput synthesis, meeting the demands of combinatorial chemistry and automated workflows.

Analytical techniques such as NMR spectroscopy, HPLC, and mass spectrometry are routinely employed to characterize Methyl 2,5-dibromothiophene-3-carboxylate, ensuring purity and consistency for research and commercial use. The compound’s spectral data and crystallographic properties are well-documented, facilitating its integration into computational chemistry models and AI-driven molecular design platforms.

As the scientific community advances toward smart materials and nanotechnology, Methyl 2,5-dibromothiophene-3-carboxylate continues to emerge as a key player. Its adaptability in polymer chemistry and supramolecular assemblies underscores its relevance in cutting-edge applications. With ongoing innovations in catalysis and reaction engineering, this compound is poised to remain at the forefront of chemical innovation.

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