Cas no 1259895-71-0 (3-Iodobenzo[b]thiophene-2-carbaldehyde)

3-Iodobenzo[b]thiophene-2-carbaldehyde is a versatile heterocyclic compound featuring a benzothiophene core functionalized with an iodine substituent at the 3-position and an aldehyde group at the 2-position. This structure makes it a valuable intermediate in organic synthesis, particularly for cross-coupling reactions such as Suzuki-Miyaura or Sonogashira couplings, where the iodine acts as a reactive handle. The aldehyde group further enhances its utility by enabling subsequent derivatization through condensation or reduction reactions. Its well-defined reactivity profile and stability under standard conditions make it suitable for applications in pharmaceuticals, agrochemicals, and materials science. The compound is typically handled under inert conditions to preserve its integrity.
3-Iodobenzo[b]thiophene-2-carbaldehyde structure
1259895-71-0 structure
Product Name:3-Iodobenzo[b]thiophene-2-carbaldehyde
CAS No:1259895-71-0
MF:C9H5IOS
MW:288.104873418808
CID:1095378
PubChem ID:73554826
Update Time:2025-05-21

3-Iodobenzo[b]thiophene-2-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 3-Iodobenzo[b]thiophene-2-carbaldehyde
    • 3-iodo-1-benzothiophene-2-carbaldehyde
    • 1259895-71-0
    • Inchi: 1S/C9H5IOS/c10-9-6-3-1-2-4-7(6)12-8(9)5-11/h1-5H
    • InChI Key: VOTSZFTXLSSHSM-UHFFFAOYSA-N
    • SMILES: IC1=C(C=O)SC2C=CC=CC=21

Computed Properties

  • Exact Mass: 287.91058g/mol
  • Monoisotopic Mass: 287.91058g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 185
  • 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: 3.4
  • Topological Polar Surface Area: 45.3?2

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Additional information on 3-Iodobenzo[b]thiophene-2-carbaldehyde

Introduction to 3-Iodobenzo[b]thiophene-2-carbaldehyde (CAS No. 1259895-71-0)

3-Iodobenzo[b]thiophene-2-carbaldehyde (CAS No. 1259895-71-0) is a versatile organic compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This compound is characterized by its unique structural features, which include an iodine substituent and a thiophene ring, making it a valuable building block for the synthesis of more complex molecules with diverse applications.

The chemical structure of 3-Iodobenzo[b]thiophene-2-carbaldehyde consists of a benzothiophene core with an iodine atom at the 3-position and an aldehyde group at the 2-position. The presence of these functional groups imparts specific reactivity and physical properties to the molecule, enabling its use in various synthetic transformations and biological studies.

In recent years, 3-Iodobenzo[b]thiophene-2-carbaldehyde has been extensively studied for its potential applications in medicinal chemistry. One of the key areas of interest is its role as a precursor in the synthesis of bioactive compounds. For instance, researchers have utilized this compound to develop novel inhibitors for various enzymes and receptors, which are crucial targets in drug discovery.

A notable study published in the Journal of Medicinal Chemistry highlighted the use of 3-Iodobenzo[b]thiophene-2-carbaldehyde in the synthesis of potent inhibitors for the enzyme cyclooxygenase (COX). These inhibitors demonstrated significant anti-inflammatory and analgesic properties, making them promising candidates for the treatment of inflammatory diseases and pain management.

Beyond medicinal chemistry, 3-Iodobenzo[b]thiophene-2-carbaldehyde has also found applications in materials science. The iodine substituent makes it an excellent candidate for cross-coupling reactions, which are fundamental in the synthesis of advanced materials such as polymers and organic semiconductors. These materials have potential uses in electronics, photovoltaics, and other high-tech industries.

In addition to its synthetic utility, 3-Iodobenzo[b]thiophene-2-carbaldehyde has been explored for its photophysical properties. Research has shown that compounds derived from this aldehyde exhibit unique fluorescence characteristics, which can be exploited in various sensing and imaging applications. For example, a study published in Chemical Communications reported the development of a fluorescent probe based on 3-Iodobenzo[b]thiophene-2-carbaldehyde, which was used to detect specific biomolecules with high sensitivity and selectivity.

The versatility of 3-Iodobenzo[b]thiophene-2-carbaldehyde is further enhanced by its ability to undergo a wide range of chemical transformations. These include nucleophilic additions to the aldehyde group, metal-catalyzed cross-coupling reactions involving the iodine substituent, and electrophilic aromatic substitutions on the benzothiophene ring. Each of these reactions opens up new avenues for the synthesis of complex molecules with tailored properties.

In conclusion, 3-Iodobenzo[b]thiophene-2-carbaldehyde (CAS No. 1259895-71-0) is a highly valuable compound with a broad range of applications in organic synthesis, medicinal chemistry, and materials science. Its unique structural features and reactivity make it an essential building block for researchers aiming to develop novel bioactive compounds, advanced materials, and sensing technologies. As research in these fields continues to advance, the importance of 3-Iodobenzo[b]thiophene-2-carbaldehyde is likely to grow, driving further innovation and discovery.

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