Cas no 34128-30-8 (methyl 3-bromobenzo[b]thiophene-2-carboxylate)

Methyl 3-bromobenzo[b]thiophene-2-carboxylate is a brominated heterocyclic ester with significant utility in organic synthesis and pharmaceutical research. Its benzo[b]thiophene scaffold, functionalized with a bromine atom at the 3-position and an ester group at the 2-position, makes it a versatile intermediate for cross-coupling reactions, such as Suzuki or Stille couplings, enabling further derivatization. The electron-withdrawing carboxylate group enhances reactivity in nucleophilic substitution reactions. This compound is particularly valuable in the development of bioactive molecules, including potential therapeutic agents, due to its structural rigidity and compatibility with diverse synthetic pathways. High purity and stability under standard conditions ensure reliable performance in research applications.
methyl 3-bromobenzo[b]thiophene-2-carboxylate structure
34128-30-8 structure
Product Name:methyl 3-bromobenzo[b]thiophene-2-carboxylate
CAS No:34128-30-8
MF:C10H7BrO2S
MW:271.130380868912
CID:2126679
PubChem ID:12238750
Update Time:2025-10-30

methyl 3-bromobenzo[b]thiophene-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • methyl 3-bromobenzo[b]thiophene-2-carboxylate
    • methyl 3-bromo-1-benzothiophene-2-carboxylate
    • DTXSID50481885
    • 34128-30-8
    • Methyl3-bromobenzo[b]thiophene-2-carboxylate
    • SCHEMBL1805430
    • DA-06673
    • XFONNRDVFHFOGX-UHFFFAOYSA-N
    • MFCD20526506
    • E91985
    • HS-6450
    • Inchi: 1S/C10H7BrO2S/c1-13-10(12)9-8(11)6-4-2-3-5-7(6)14-9/h2-5H,1H3
    • InChI Key: XFONNRDVFHFOGX-UHFFFAOYSA-N
    • SMILES: BrC1=C(C(=O)OC)SC2C=CC=CC=21

Computed Properties

  • Exact Mass: 269.93501g/mol
  • Monoisotopic Mass: 269.93501g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 234
  • 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: 3.8
  • Topological Polar Surface Area: 54.5?2

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abcr
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Methyl 3-bromobenzo[b]thiophene-2-carboxylate; .
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Additional information on methyl 3-bromobenzo[b]thiophene-2-carboxylate

Introduction to Methyl 3-Bromobenzo[b]Thiophene-2-Carboxylate (CAS No: 34128-30-8)

Methyl 3-bromobenzo[b]thiophene-2-carboxylate, identified by the CAS number 34128-30-8, is a significant compound in the field of organic chemistry. This compound belongs to the class of benzo[b]thiophenes, which are heterocyclic aromatic compounds with a sulfur atom in the ring. The presence of a bromine substituent at the 3-position and a methyl ester group at the 2-position makes this compound unique and versatile for various applications.

The structure of methyl 3-bromobenzo[b]thiophene-2-carboxylate consists of a benzo[b]thiophene core, where a benzene ring is fused to a thiophene ring. The bromine atom at the 3-position introduces electron-withdrawing effects, which can influence the electronic properties of the molecule. The methyl ester group at the 2-position adds functionality, making it suitable for further chemical modifications. This compound is widely studied for its potential in material science, pharmaceuticals, and optoelectronic devices.

Recent studies have highlighted the importance of benzo[b]thiophenes in the development of advanced materials. For instance, researchers have explored the use of methyl 3-bromobenzo[b]thiophene-2-carboxylate as a precursor for synthesizing novel semiconducting polymers. These polymers exhibit excellent charge transport properties, making them ideal for applications in organic field-effect transistors (OFETs) and photovoltaic devices.

The synthesis of methyl 3-bromobenzo[b]thiophene-2-carboxylate involves multi-step organic reactions, including Friedel-Crafts alkylation and esterification. The choice of reagents and reaction conditions plays a crucial role in achieving high yields and purity. Recent advancements in catalytic methods have enabled more efficient and selective synthesis pathways, reducing production costs and environmental impact.

In terms of applications, methyl 3-bromobenzo[b]thiophene-2-carboxylate has shown promise in drug discovery. Its unique electronic properties make it a potential candidate for designing bioactive molecules targeting specific diseases. For example, studies have demonstrated that derivatives of this compound exhibit anti-inflammatory and anticancer activities, paving the way for further exploration in medicinal chemistry.

The optical properties of methyl 3-bromobenzo[b]thiophene-2-carboxylate are another area of active research. Its absorption spectrum in the visible region makes it suitable for applications in light-emitting diodes (LEDs) and sensors. Researchers have also investigated its ability to act as a photosensitizer in photodynamic therapy, leveraging its light-responsive characteristics for therapeutic purposes.

From an environmental perspective, understanding the degradation pathways of methyl 3-bromobenzo[b]thiophene-2-carboxylate is crucial for assessing its ecological impact. Studies have shown that this compound undergoes biodegradation under specific conditions, reducing its persistence in natural systems. However, further research is needed to optimize waste management practices and minimize environmental risks.

In conclusion, methyl 3-bromobenzo[b]thiophene-2-carboxylate (CAS No: 34128-30-8) is a versatile compound with diverse applications across multiple disciplines. Its unique chemical structure and functional groups make it an attractive target for researchers aiming to develop innovative materials and therapies. As advancements in synthetic methods and application studies continue to emerge, this compound is poised to play an increasingly important role in both academic and industrial settings.

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