Cas no 120759-16-2 (5-bromo-2-chloro-3-Thiophenecarboxaldehyde)

5-Bromo-2-chloro-3-thiophenecarboxaldehyde is a heterocyclic aldehyde compound featuring both bromo and chloro substituents on a thiophene ring. This highly functionalized derivative serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and materials science applications. The presence of multiple halogen groups enhances its reactivity in cross-coupling reactions, such as Suzuki or Stille couplings, while the aldehyde functionality allows for further derivatization via condensation or reduction. Its well-defined structure and stability under standard conditions make it a reliable building block for constructing complex thiophene-based scaffolds. The compound is typically handled under inert conditions to preserve its reactivity.
5-bromo-2-chloro-3-Thiophenecarboxaldehyde structure
120759-16-2 structure
Product Name:5-bromo-2-chloro-3-Thiophenecarboxaldehyde
CAS No:120759-16-2
MF:C5H2BrClOS
MW:225.490778446198
CID:2135822
PubChem ID:12614611
Update Time:2025-05-28

5-bromo-2-chloro-3-Thiophenecarboxaldehyde Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-2-chloro-3-Thiophenecarboxaldehyde
    • 5-bromo-2-chlorothiophene-3-carbaldehyde
    • DA-37857
    • DTXSID70504409
    • 120759-16-2
    • SCHEMBL154875
    • VEA75916
    • DTXCID60455219
    • Inchi: 1S/C5H2BrClOS/c6-4-1-3(2-8)5(7)9-4/h1-2H
    • InChI Key: PYESNBLXILKHCY-UHFFFAOYSA-N
    • SMILES: BrC1=CC(C=O)=C(S1)Cl

Computed Properties

  • Exact Mass: 223.86983g/mol
  • Monoisotopic Mass: 223.86983g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 122
  • 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: 3.1
  • Topological Polar Surface Area: 45.3?2

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5-bromo-2-chloro-3-Thiophenecarboxaldehyde Related Literature

Additional information on 5-bromo-2-chloro-3-Thiophenecarboxaldehyde

Comprehensive Overview of 5-Bromo-2-chloro-3-Thiophenecarboxaldehyde (CAS No. 120759-16-2): Properties, Applications, and Industry Trends

The chemical compound 5-bromo-2-chloro-3-thiophenecarboxaldehyde (CAS No. 120759-16-2) is a halogenated thiophene derivative with significant relevance in pharmaceutical and material science research. Characterized by its bromo and chloro substituents on the thiophene ring, this aldehyde serves as a versatile intermediate in organic synthesis. Its molecular structure (C5H2BrClOS) combines reactivity with stability, making it invaluable for constructing complex heterocycles.

Recent interest in 5-bromo-2-chloro-3-thiophenecarboxaldehyde has surged due to its role in developing OLED materials and small-molecule drugs. As industries prioritize sustainable chemistry, researchers explore greener synthetic routes for such halogenated thiophenes. Questions like "How to optimize the yield of 5-bromo-2-chloro-3-thiophenecarboxaldehyde?" or "What are alternatives to palladium catalysts in its derivatization?" reflect current academic and industrial focus areas.

From a technical perspective, the compound’s carboxaldehyde group enables condensation reactions, while its halogen atoms facilitate cross-coupling methodologies like Suzuki or Stille reactions. This dual functionality aligns with the growing demand for multifunctional building blocks in medicinal chemistry, particularly for kinase inhibitor design. Analytical techniques such as HPLC and NMR are critical for purity assessment, addressing common queries about quality control protocols.

Emerging applications include its use in conductive polymers for flexible electronics—a hotspot tied to the Internet of Things (IoT) revolution. The compound’s electron-withdrawing properties enhance charge transport in organic semiconductors, a topic frequently searched alongside terms like "thiophene-based electronic materials". Environmental considerations also drive innovation; labs now investigate biodegradable catalysts for its production to reduce waste.

In summary, 5-bromo-2-chloro-3-thiophenecarboxaldehyde exemplifies the intersection of traditional organic synthesis and cutting-edge technology. Its adaptability across disciplines—from drug discovery to renewable energy materials—ensures enduring scientific and commercial interest, reinforced by rigorous structure-activity relationship (SAR) studies and process optimization efforts.

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