5-Bromo-7-azaindole
[CAS# 183208-35-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 5-Bromo-7-azaindole
• Synonyms: 5-Bromo-1H-pyrrolo[2,3-b]pyridine
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.03
• CAS Registry Number: 183208-35-7
• EC Number: 629-247-8
• SMILES: C1=CNC2=NC=C(C=C21)Br

Properties

• Melting point: 169-179 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H411

Discovery and Applications

5-Bromo-7-azaindole is a halogenated heterocyclic compound with notable chemical and pharmacological significance. As a derivative of azaindole, it incorporates both a bromine atom and a nitrogen-containing ring structure, which endows it with unique reactivity and properties.

The discovery of 5-bromo-7-azaindole is tied to research into heterocyclic compounds and their potential applications in various fields. The addition of a bromine atom to the 5-position of the azaindole ring enhances the molecule's reactivity, making it a valuable intermediate in organic synthesis. The 7-azaindole ring, which includes a nitrogen atom within an indole-like structure, imparts stability and contributes to the molecule's ability to engage in diverse chemical reactions.

One of the primary applications of 5-bromo-7-azaindole is in medicinal chemistry. The compound serves as a crucial building block for the synthesis of various pharmaceutical agents. Its structure allows for modifications that can lead to the development of novel drugs with specific biological activities. For instance, derivatives of 5-bromo-7-azaindole have been investigated for their potential as kinase inhibitors, which are important in the treatment of cancer and other diseases.

In addition to its role in drug discovery, 5-bromo-7-azaindole is used in the development of advanced materials and functionalized polymers. The bromine atom in the compound provides a reactive site that can be utilized in polymerization reactions or in the synthesis of complex materials. These materials often find applications in electronic devices, sensors, and other high-tech areas where specific chemical properties are required.

Furthermore, 5-bromo-7-azaindole is employed in chemical research as a reagent and intermediate. Its unique combination of bromine and nitrogen-containing ring systems makes it a versatile tool in the synthesis of more complex organic molecules. Researchers use it to explore new chemical pathways and to develop innovative compounds with potential applications in various industries.

References

2023. Screening of small molecule compounds targeting hnRNPA2 protein. Medicinal Chemistry Research.
DOI: 10.1007/s00044-023-03155-2

2020. Synthesis and biological evaluation of selected 7-azaindole derivatives as CDK9/Cyclin T and Haspin inhibitors. Medicinal Chemistry Research.
DOI: 10.1007/s00044-020-02560-1

2013. Insight into the toxic effects of cis-dichloridoplatinum(II) complexes containing 7-azaindole halogeno derivatives in tumor cells. Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry.
DOI: 10.1007/s00775-013-1003-7