5-Azaindole
[CAS 271-34-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 5-Azaindole
• Synonyms: 1H-Pyrrolo[3,2-c]pyridine
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• CAS Registry Number: 271-34-1
• EC Number: 676-348-8
• SMILES: C1=CNC2=C1C=NC=C2

Properties

• Melting point: 113 °C

Safety Data

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

Hazard Classification

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

chemBlink Chemical Story

5-Azaindole, also known as 5-aza-1H-indole, is a heterocyclic compound where one carbon atom in the indole ring system is replaced by a nitrogen atom. Its chemical formula is C₇H₅N₂. This compound is notable for its distinctive chemical structure and its diverse range of applications in various scientific fields.

The discovery of 5-azaindole dates back to the early 20th century when chemists were investigating the modification of indole derivatives. By substituting a carbon atom in the indole ring with nitrogen, researchers were able to create 5-azaindole, which exhibited new chemical properties and reactivity profiles compared to its parent compound. This substitution alters the electronic distribution within the molecule, making it a valuable compound for further study.

In medicinal chemistry, 5-azaindole has gained prominence as a versatile scaffold in drug development. The nitrogen atom in the ring contributes to its ability to interact with biological targets, which can influence the efficacy and specificity of drug candidates. Researchers have explored 5-azaindole derivatives for their potential as inhibitors or modulators of various biological pathways. For instance, some derivatives have shown promise in targeting protein kinases, enzymes involved in numerous cellular processes and disease states.

In addition to its role in pharmaceuticals, 5-azaindole is used in material science, particularly in the development of organic electronic materials. Its ability to participate in charge transfer processes makes it suitable for use in organic light-emitting diodes (OLEDs) and organic photovoltaic cells. The presence of the nitrogen atom in the ring system can enhance the electronic properties of the material, improving device performance.

Moreover, 5-azaindole serves as an important intermediate in organic synthesis. Its chemical reactivity allows it to be employed in the creation of more complex molecules. This versatility is useful for producing a wide range of compounds used in research and industry.

Research into 5-azaindole continues as scientists explore its potential applications in new areas, including catalysis and advanced materials. Its unique structure and properties make it a compound of significant interest for ongoing scientific investigation.

References

2023. Synthesis and Preclinical Evaluation of Fluorinated 5-Azaindoles as CB2 PET Radioligands. ACS Chemical Neuroscience, 14(15).
DOI: 10.1021/acschemneuro.3c00345

2022. Regioselectivity in inhibition of peptide deformylase from Haemophilus influenzae by 4- vs 5-azaindole hydroxamic acid derivatives: Biochemical, structural and antimicrobial studies. Bioorganic Chemistry, 128.
DOI: 10.1016/j.bioorg.2022.106095

2022. Development of Azaindole-Based Frameworks as Potential Antiviral Agents and Their Future Perspectives. Journal of Medicinal Chemistry, 65(9).
DOI: 10.1021/acs.jmedchem.2c00444