Cas no 37815-80-8 (5-Bromothiophene-2,3-dicarbaldehyde)

5-Bromothiophene-2,3-dicarbaldehyde is a brominated thiophene derivative featuring two aldehyde functional groups at the 2- and 3-positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of heterocyclic compounds and functionalized thiophene derivatives. The presence of both bromine and aldehyde groups allows for selective modifications, enabling applications in pharmaceuticals, agrochemicals, and materials science. Its well-defined reactivity profile facilitates cross-coupling reactions, condensation processes, and further derivatization. The compound is characterized by high purity and stability, making it suitable for demanding synthetic applications. Its structural features are advantageous for constructing complex molecular architectures with precision.
5-Bromothiophene-2,3-dicarbaldehyde structure
37815-80-8 structure
Product Name:5-Bromothiophene-2,3-dicarbaldehyde
CAS No:37815-80-8
MF:C6H3BrO2S
MW:219.055819749832
CID:2950327
PubChem ID:84819467
Update Time:2025-08-04

5-Bromothiophene-2,3-dicarbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 5-溴噻吩-2,3-二甲醛
    • 5-Bromothiophene-2,3-dicarbaldehyde
    • 5-Bromo-2,3-thiophenedicarboxaldehyde
    • 37815-80-8
    • CJALNXQQXPYSRB-UHFFFAOYSA-N
    • SCHEMBL4442166
    • Inchi: 1S/C6H3BrO2S/c7-6-1-4(2-8)5(3-9)10-6/h1-3H
    • InChI Key: CJALNXQQXPYSRB-UHFFFAOYSA-N
    • SMILES: BrC1=CC(C=O)=C(C=O)S1

Computed Properties

  • Exact Mass: 217.90371g/mol
  • Monoisotopic Mass: 217.90371g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 151
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.9
  • Topological Polar Surface Area: 62.4

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Additional information on 5-Bromothiophene-2,3-dicarbaldehyde

5-Bromothiophene-2,3-dicarbaldehyde (CAS No. 37815-80-8): A Versatile Building Block in Modern Chemical Biology and Medicinal Chemistry

5-Bromothiophene-2,3-dicarbaldehyde, identified by its Chemical Abstracts Service (CAS) number CAS No. 37815-80-8, is a highly significant compound in the realm of chemical biology and medicinal chemistry. This heterocyclic aromatic aldehyde features a thiophene core substituted with two aldehyde groups and a bromine atom, making it a valuable intermediate for the synthesis of complex organic molecules. Its unique structural attributes have positioned it as a cornerstone in the development of novel pharmaceuticals, agrochemicals, and advanced materials.

The< strong> thiophene ring in 5-Bromothiophene-2,3-dicarbaldehyde contributes to its remarkable electronic properties, which are influenced by the electron-withdrawing nature of the aldehyde groups and the electron-donating effect of the bromine atom. This balance of electronic characteristics makes it an ideal candidate for constructing diverse molecular architectures, including pharmacophores that exhibit potent biological activity. The< strong> aldehyde functionality further enhances its utility as a synthetic precursor, enabling condensation reactions with a wide range of nucleophiles to form Schiff bases, imines, and other functional derivatives.

In recent years, the< strong> pharmaceutical industry has shown increasing interest in thiophene-based compounds due to their prevalence in biologically active molecules. For instance, several FDA-approved drugs contain thiophene scaffolds, highlighting their therapeutic potential. Among these, 5-Bromothiophene-2,3-dicarbaldehyde has been extensively utilized in the synthesis of kinase inhibitors, antiviral agents, and anti-inflammatory compounds. Its ability to serve as a cross-coupling partner in palladium-catalyzed reactions has also facilitated the construction of more complex heterocyclic systems, expanding its applications in drug discovery.

The< strong> synthetic versatility of 5-Bromothiophene-2,3-dicarbaldehyde is further underscored by its role in material science. Researchers have leveraged this compound to develop organic semiconductors and luminescent materials due to its ability to form stable π-conjugated systems. These materials are critical for applications in optoelectronics, such as organic light-emitting diodes (OLEDs) and photovoltaic cells. The< strong> bromine substituent also allows for further functionalization via metal-halogen exchange reactions, enabling the creation of polymers and copolymers with tailored properties.

Advances in computational chemistry have enhanced our understanding of how 5-Bromothiophene-2,3-dicarbaldehyde interacts with biological targets. Molecular modeling studies have revealed that its< strong> aldehyde groups can form hydrogen bonds with key residues in protein active sites, while the< strong> thiophene ring can stack with aromatic residues. This insight has guided the rational design of analogs with improved binding affinities and selectivity. Additionally, crystallographic analyses of complexes formed with enzymes have provided detailed structural information that informs the development of next-generation inhibitors.

The< strong> agrochemical sector has also benefited from the incorporation of 5-Bromothiophene-2,3-dicarbaldehyde into novel pesticide formulations. Its structural features contribute to enhanced bioavailability and reduced environmental persistence compared to traditional agrochemicals. By serving as a precursor for herbicides and fungicides, this compound plays a crucial role in sustainable agriculture practices aimed at maximizing crop yields while minimizing ecological impact.

In conclusion, 5-Bromothiophene-2,3-dicarbaldehyde (CAS No. 37815-80-8) is a multifaceted compound with far-reaching implications across multiple scientific disciplines. Its unique combination of functional groups makes it an indispensable tool for synthetic chemists working on pharmaceuticals, materials science, and agrochemicals. As research continues to uncover new applications for this versatile intermediate, its importance is only expected to grow in the coming years.

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