2-Bromoimidazo[1,2-a]pyridine
[CAS# 112581-95-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 2-Bromoimidazo[1,2-a]pyridine
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.03
• CAS Registry Number: 112581-95-0
• EC Number: 813-437-4
• SMILES: C1=CC2=NC(=CN2C=C1)Br

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2-Bromoimidazo[1,2-a]pyridine is a heterocyclic compound that occupies an important position in organic chemistry and medicinal chemistry. The structural feature of 2-Bromoimidazo[1,2-a]pyridine is that the imidazole ring is fused to the pyridine ring and a bromine atom is located at the 2-position. This compound was originally discovered during the synthesis of new molecules with potential biological activity.

The synthesis of 2-Bromoimidazo[1,2-a]pyridine usually involves the cyclization of suitable precursors. A common synthetic route involves the reaction of 2-aminopyridine with α-haloketone under specific conditions to form the imidazo[1,2-a]pyridine core. The bromine atom is introduced by a subsequent bromination reaction to obtain the 2-bromo derivative.

2-Bromoimidazo[1,2-a]pyridine shows great potential in various applications, especially in medicinal chemistry and materials science. Its fused heterocyclic structure makes it a versatile scaffold for drug development and other applications.

The most notable application of 2-Bromoimidazo[1,2-a]pyridine is drug development. This compound is a core structure for the synthesis of various bioactive molecules, including kinase inhibitors, which are essential for cancer treatment. The presence of bromine atoms enhances its reactivity, allowing for further functionalization and optimization of pharmacological properties.

Studies have shown that 2-bromoimidazo[1,2-a]pyridine derivatives have significant antimicrobial activity. These compounds have been tested against various bacterial and fungal strains, showing potential as therapeutic agents for treating infections, especially those caused by drug-resistant pathogens.

In addition to medicinal chemistry, 2-bromoimidazo[1,2-a]pyridine has applications in materials science. Its unique electronic properties make it suitable for the design of organic semiconductors and other advanced materials. This compound can help develop new materials with specific electrical and optical properties.

Ongoing research on 2-bromoimidazo[1,2-a]pyridine is expected to further explore its potential in various fields. Future studies may focus on optimizing its synthesis, improving its pharmacokinetic properties, and exploring its utility in new therapeutic areas. In addition, the development of novel derivatives and analogs can expand its applications in medicinal chemistry and materials science.

References

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