6-Azaindole
[CAS# 271-29-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 6-Azaindole
• Synonyms: 1H-Pyrrolo[2,3-c]pyridine
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• CAS Registry Number: 271-29-4
• EC Number: 664-233-5
• SMILES: C1=CNC2=C1C=CN=C2

Properties

• Melting point: 136-137 ºC

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H315-H318-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

6-Azaindole, with the chemical formula C₇H₅N₃, is a heterocyclic compound characterized by a fused ring system consisting of an indole framework with a nitrogen atom replacing one of the carbon atoms in the six-membered ring. This compound has garnered attention for its unique chemical properties and versatile applications in various fields.

The discovery of 6-azaindole can be traced back to the early 20th century, when chemists were exploring the chemical behavior of indole derivatives. The introduction of nitrogen into the indole ring system altered its electronic and steric properties, leading to the synthesis of 6-azaindole. Its development was part of a broader effort to create novel heterocyclic compounds with specific reactivity and functionality.

In pharmaceuticals, 6-azaindole has found several significant applications. Its structure allows for interactions with biological targets, making it a valuable scaffold in drug discovery. It has been used as an intermediate in the synthesis of various pharmaceutical agents, particularly those aimed at treating neurological and psychiatric disorders. The presence of the nitrogen atom in the ring system can influence the binding affinity and specificity of drug candidates.

In addition to its pharmaceutical applications, 6-azaindole is employed in material science. Its unique electronic properties make it useful in the development of organic electronic materials. For example, it has been investigated for use in organic light-emitting diodes (OLEDs) and organic photovoltaic cells, where its ability to participate in charge transfer processes can enhance device performance.

Furthermore, 6-azaindole is utilized as a building block in the synthesis of other complex molecules. Its chemical reactivity allows it to participate in a variety of transformations, enabling the creation of diverse compounds for research and industrial purposes.

Research into 6-azaindole continues, particularly in exploring its potential applications in new areas such as catalysis and materials science. Its ability to modify chemical properties through substitution and functionalization makes it a compound of interest for ongoing scientific investigation.