Cas no 1427358-09-5 (5,7-Dibromoimidazo[1,5-a]pyridine)

5,7-Dibromoimidazo[1,5-a]pyridine is a brominated heterocyclic compound featuring an imidazo[1,5-a]pyridine core structure. This derivative is notable for its utility as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and functional materials. The presence of bromine atoms at the 5- and 7-positions enhances its reactivity, facilitating further functionalization via cross-coupling reactions such as Suzuki or Buchwald-Hartwig couplings. Its rigid fused-ring system contributes to stability while offering potential for π-stacking interactions, making it valuable in materials science. The compound is typically handled under controlled conditions due to its sensitivity. High-purity grades ensure consistent performance in research and industrial applications.
5,7-Dibromoimidazo[1,5-a]pyridine structure
1427358-09-5 structure
Product Name:5,7-Dibromoimidazo[1,5-a]pyridine
CAS No:1427358-09-5
MF:C7H4Br2N2
MW:275.928059577942
MDL:MFCD23711212
CID:4598841
PubChem ID:92134881
Update Time:2025-10-21

5,7-Dibromoimidazo[1,5-a]pyridine Chemical and Physical Properties

Names and Identifiers

    • 5,7-Dibromoimidazo[1,5-a]pyridine
    • CHC35809
    • O11330
    • MFCD23711212
    • 1427358-09-5
    • AS-50205
    • CS-0183133
    • SCHEMBL19534180
    • AKOS027325384
    • DB-397731
    • MDL: MFCD23711212
    • Inchi: 1S/C7H4Br2N2/c8-5-1-6-3-10-4-11(6)7(9)2-5/h1-4H
    • InChI Key: ARKLZBXBOGURCZ-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=CC2=CN=CN21)Br

Computed Properties

  • Exact Mass: 275.87207g/mol
  • Monoisotopic Mass: 273.87412g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 153
  • 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: 3.6
  • Topological Polar Surface Area: 17.3

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Additional information on 5,7-Dibromoimidazo[1,5-a]pyridine

5,7-Dibromoimidazo[1,5-a]pyridine: A Comprehensive Overview

The compound with CAS No. 1427358-09-5, known as 5,7-Dibromoimidazo[1,5-a]pyridine, is a fascinating molecule that has garnered significant attention in the fields of organic chemistry and materials science. This compound belongs to the class of imidazo[1,5-a]pyridines, which are heterocyclic aromatic compounds with unique electronic properties. The presence of bromine atoms at the 5 and 7 positions introduces additional functionality, making this compound particularly interesting for various applications.

Imidazo[1,5-a]pyridines are known for their ability to act as building blocks in the synthesis of more complex molecules. The bromination at the 5 and 7 positions in 5,7-Dibromoimidazo[1,5-a]pyridine enhances its reactivity and opens up new possibilities for chemical transformations. Recent studies have explored the use of this compound in the development of advanced materials, such as organic semiconductors and light-emitting diodes (LEDs). Its electronic properties make it a promising candidate for applications in optoelectronics.

The synthesis of 5,7-Dibromoimidazo[1,5-a]pyridine involves a multi-step process that typically begins with the preparation of the parent imidazo[1,5-a]pyridine structure. Bromination is then achieved through electrophilic substitution reactions under controlled conditions. Researchers have optimized these conditions to achieve high yields and purity levels, ensuring that the compound is suitable for downstream applications.

One of the most intriguing aspects of 5,7-Dibromoimidazo[1,5-a]pyridine is its ability to undergo various post-synthetic modifications. For instance, substitution reactions at the brominated positions can lead to the incorporation of functional groups that tailor the molecule's properties for specific uses. This flexibility has made it a valuable tool in drug discovery efforts, where fine-tuning molecular structures is crucial for achieving desired biological activities.

Recent advancements in computational chemistry have provided deeper insights into the electronic structure of 5,7-Dibromoimidazo[1,5-a]pyridine. Density functional theory (DFT) calculations have revealed that the bromine atoms significantly influence the molecule's frontier molecular orbitals (FMOs), which are critical for its reactivity and electronic behavior. These findings have been instrumental in guiding experimental studies aimed at optimizing its performance in electronic devices.

In terms of applications, 5,7-Dibromoimidazo[1,5-a]pyridine has shown potential in the field of sensors and biosensors due to its sensitivity to environmental changes such as pH and temperature. Its ability to act as a fluorescent probe makes it a valuable tool in analytical chemistry and biomedical research. Additionally, its use in catalysis has been explored, with reports suggesting that it can serve as an efficient catalyst in certain organic transformations.

The growing interest in Imidazo[1,5-a]pyridines derivatives has led to an increase in collaborative research efforts across academic and industrial settings. Scientists are now focusing on scaling up the synthesis of 5,7-Dibromoimidazo[1,5-a]pyridine to meet the demands of large-scale applications. This includes developing cost-effective synthesis routes and improving process efficiency to ensure sustainability.

In conclusion, CAS No. 1427358-09-5, or 5,7-Dibromoimidazo[1,5-a]pyridine, represents a versatile compound with a wide range of potential applications. Its unique electronic properties and functionalizability make it a valuable asset in modern chemistry and materials science. As research continues to uncover new possibilities for this compound

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