5-Bromo-4,7-diazaindole
[CAS# 875781-43-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 5-Bromo-4,7-diazaindole
• Synonyms: 2-Bromo-5H-pyrrolo[2,3-b]pyrazine
• Molecular Formula: C₆H₄BrN₃
• Molecular Weight: 198.02
• CAS Registry Number: 875781-43-4
• EC Number: 851-148-5
• SMILES: C1=CNC2=NC=C(N=C21)Br

Properties

• Density: 2.00
• Boiling point: 265 °C
• Flash point: 114 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

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
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

5-Bromo-4,7-diazaindole, which has one bromine atom and two nitrogen atoms within the indole skeleton, has attracted interest for its properties and potential uses in various scientific fields. The compound was first synthesized during the late 20th century during the study of modified indole derivatives. Scientists were exploring how to change its chemical properties and reactivity by substituting different atoms in the indole ring. The introduction of bromine and nitrogen into the indole ring produced 5-bromo-4,7-diazaindole, which exhibits different chemical behavior compared to other indole derivatives. Its discovery was a key step in understanding the effects of halogen and nitrogen substitution on indole chemistry.

5-Bromo-4,7-diazaindole is widely used as a building block in organic synthesis. The presence of bromine and nitrogen makes it a valuable intermediate in making a range of complex organic molecules. Chemists use it to synthesize drugs, agrochemicals, and other fine chemicals, taking advantage of its reactivity to build a variety of structures.

In medicinal chemistry, this compound is being explored for potential therapeutic applications. Its unique structure can be used to design and develop new drugs with specific biological activities. Researchers use its modified indole core to study its efficacy in treating various diseases and conditions to create novel pharmaceutical agents.

The properties of this compound are also studied in materials science. Its unique structure and reactivity can be used to develop advanced materials with special electronic or optical properties. It can serve as a precursor for the synthesis of materials for electronic devices or other high-tech applications.

In biochemical research, 5-bromo-4,7-diazaindole is used to study the role of indole derivatives in biological systems. Its interaction with biomolecules can provide insights into enzyme mechanisms, protein interactions, and other biochemical processes, contributing to a deeper understanding of molecular biology.

References

2015. Fragment-based discovery of potent ERK2 pyrrolopyrazine inhibitors. Bioorganic & Medicinal Chemistry Letters, 25(21).
DOI: 10.1016/j.bmcl.2015.08.048