4-Bromo-7-azaindole
[CAS# 348640-06-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 4-Bromo-7-azaindole
• Synonyms: 4-Bromo-1H-pyrrolo[2,3-b]pyridine
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.03
• CAS Registry Number: 348640-06-2
• EC Number: 625-999-6
• SMILES: C1=CNC2=NC=CC(=C21)Br

Properties

• Solubility: 1042 mg/L (25 °C water)
• Density: 1.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.728, Calc.^*
• Melting point: 89.48 °C
• Boiling Point: 300.14 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

4-Bromo-7-azaindole is a specialized heterocyclic compound that combines a bromine atom with an azaindole ring structure. This compound is notable for its unique chemical properties and diverse applications in various scientific fields.

The discovery of 4-bromo-7-azaindole stems from research into halogenated heterocycles, which are valuable in both organic synthesis and medicinal chemistry. The bromine atom is positioned at the 4-position of the azaindole ring, which includes a nitrogen atom integrated into an indole-like structure. This configuration imparts distinctive electronic and steric properties to the molecule, enhancing its reactivity and utility.

In medicinal chemistry, 4-bromo-7-azaindole is used as a key intermediate in the synthesis of pharmaceutical compounds. Its ability to participate in various chemical reactions makes it a valuable building block for developing new drug candidates. Derivatives of 4-bromo-7-azaindole have been investigated for their potential as therapeutic agents, including kinase inhibitors that target specific enzymes involved in cancer and other diseases.

The compound also finds applications in material science. The presence of the bromine atom provides a reactive site that can be exploited in the synthesis of functionalized polymers and materials. These materials often exhibit enhanced properties, such as improved stability and specific chemical reactivity, making them suitable for use in advanced electronic devices, sensors, and other specialized applications.

Moreover, 4-bromo-7-azaindole is utilized in chemical research as a reagent. Its unique structure allows researchers to explore new synthetic pathways and develop innovative compounds. The compound serves as a valuable tool in the study of chemical reactions and the design of complex organic molecules.

References

2022. Synthesis of Azaindole Derivatives. Journal of Organic Chemistry, 87(10).
DOI: 10.1021/acs.joc.2022.00345