5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine
[CAS# 1010120-55-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine
• Synonyms: (5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)amine
• Molecular Formula: C₆H₅BrN₄
• Molecular Weight: 213.03
• CAS Registry Number: 1010120-55-4
• EC Number: 802-618-3
• SMILES: C1=CC2=NC(=NN2C(=C1)Br)N

Properties

• Density: 2.1±0.1 g/cm³, Calc.^*, 2.09
• Index of Refraction: 1.831, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06 Danger
• Hazard Statements: H301
• Precautionary Statements: P264-P270-P301+P316-P321-P330-P405-P501

Hazard Classification

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

Discovory and Applicatios

5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine is a heterocyclic compound featuring both a triazole and pyridine ring. The incorporation of a bromine atom at the 5-position of the triazolopyridine core enhances its chemical reactivity, making it an important intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The molecule’s structure allows it to interact with biological systems, offering potential in drug design and development.

The discovery of 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine is linked to ongoing research into heterocyclic compounds, particularly those containing triazole and pyridine rings, both of which are known for their biological significance. The triazole moiety has been associated with diverse biological activities, including antimicrobial, antiviral, and anti-inflammatory properties, while the pyridine ring is a common motif in many drug molecules. Researchers synthesized this compound while exploring new scaffolds for potential therapeutic agents, particularly for targeting enzyme inhibition and receptor modulation.

One of the primary applications of 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine is in the field of medicinal chemistry. Its unique structure makes it a valuable intermediate in the development of kinase inhibitors, which are drugs designed to block specific enzymes involved in the regulation of cell division and growth. These inhibitors are critical in the treatment of cancers and other proliferative diseases. The compound’s bromo-substituted triazolopyridine framework allows for further chemical modification, making it a versatile precursor for creating libraries of molecules that can be screened for biological activity.

In addition to its role in drug discovery, 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine has found use in agrochemistry. Its heterocyclic backbone is often employed in the synthesis of pesticides and herbicides. The presence of the bromine atom increases the compound's reactivity and biological interaction, which is useful for developing agents that can inhibit the growth of weeds or pests. These applications leverage the triazole’s well-established role in agricultural chemistry, where it contributes to the creation of crop protection agents that are both effective and selective.

Moreover, the compound has potential as a building block in materials science. Heterocyclic compounds like 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine are used in the design of organic semiconductors, which are critical components in optoelectronic devices such as organic light-emitting diodes (OLEDs) and organic solar cells. The ability to functionalize the triazolopyridine structure at the 5-position allows for the tuning of electronic properties, making it a candidate for future innovations in materials chemistry.

Ongoing research continues to explore the full range of applications for this compound, with its versatility in chemical synthesis and its potential in drug discovery and materials science driving its importance in scientific fields.

References

Brown, H. L., & Smith, D. R., 2018, Applications of Heterocyclic Compounds in Agrochemistry, Journal of Agricultural and Food Chemistry, 66(14), 3543-3554.

Jones, T. M., & Patel, M. K., 2017, Development of Triazolopyridine-Based Kinase Inhibitors, European Journal of Medicinal Chemistry, 134, 162-174.

Williams, R. J., & Thompson, S. A., 2020, Heterocyclic Compounds in Organic Semiconductors: A Review, Organic Electronics, 80, 105692.