5-Bromo-4-fluoro-1-methyl-1h-indazole
[CAS# 1784678-61-0]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indazoles
• Name: 5-Bromo-4-fluoro-1-methyl-1h-indazole
• Molecular Formula: C₈H₆BrFN₂
• Molecular Weight: 229.05
• CAS Registry Number: 1784678-61-0
• SMILES: CN1C2=C(C=N1)C(=C(C=C2)Br)F

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.643, Calc.^*
• Boiling Point: 293.4±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 131.3±21.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P312-P330-P501

Discovory and Applicatios

5-Bromo-4-fluoro-1-methyl-1H-indazole is an organic compound classified as a halogenated indazole derivative. This compound features a benzene ring fused with a pyrazole ring, with bromine and fluorine atoms attached at the 5- and 4-positions, respectively, and a methyl group at the 1-position. The unique combination of halogen and methyl substituents on the indazole core structure imparts specific properties, which make it an important building block in organic synthesis.

The discovery of 5-bromo-4-fluoro-1-methyl-1H-indazole stems from the broader exploration of halogenated indazole derivatives, which have attracted significant attention due to their versatile reactivity and potential biological activity. Indazoles are a class of heterocyclic compounds that have been extensively studied for their role in drug development, particularly in the design of novel therapeutic agents. The introduction of halogens, such as bromine and fluorine, enhances the stability and reactivity of these compounds, enabling more efficient chemical transformations and improving their ability to interact with biological targets.

One of the primary applications of 5-bromo-4-fluoro-1-methyl-1H-indazole is in the development of pharmaceutical agents. The indazole core is found in a variety of biologically active molecules, and the presence of bromine and fluorine substituents can significantly impact the pharmacological properties of these compounds. For example, the introduction of a fluorine atom can increase the compound's lipophilicity and metabolic stability, making it more suitable for oral administration. Additionally, the bromine atom can improve the selectivity and potency of the compound by influencing its interactions with specific biological targets, such as enzymes, receptors, or ion channels. As a result, 5-bromo-4-fluoro-1-methyl-1H-indazole serves as an important intermediate in the synthesis of potential drug candidates for a variety of therapeutic areas, including cancer, neurodegenerative diseases, and infectious diseases.

Beyond its pharmaceutical applications, 5-bromo-4-fluoro-1-methyl-1H-indazole is also used in the field of materials science. The fluorine and bromine substituents on the indazole ring can modify the compound's electronic properties, making it a valuable building block in the design of organic semiconductors and materials for optoelectronic devices. The ability to fine-tune the electronic structure of the compound by introducing different halogens allows researchers to optimize its performance in electronic applications, such as organic light-emitting diodes (OLEDs), solar cells, and field-effect transistors (FETs).

In addition, the compound is useful in the synthesis of dyes and pigments, particularly those with applications in the textile and coatings industries. The halogenated indazole derivatives can exhibit unique color properties and enhanced stability compared to unmodified compounds. This makes 5-bromo-4-fluoro-1-methyl-1H-indazole a potential candidate for use in high-performance dye formulations, where factors like lightfastness, chemical stability, and color intensity are crucial.

Another promising application of 5-bromo-4-fluoro-1-methyl-1H-indazole is in the field of catalysis. The halogenated structure of the compound can be utilized in the development of new catalytic systems for organic synthesis, such as those involved in cross-coupling reactions or other metal-catalyzed transformations. The halogen atoms can enhance the coordination properties of the compound, improving its ability to interact with transition metal catalysts and facilitating efficient catalytic processes.

In conclusion, 5-bromo-4-fluoro-1-methyl-1H-indazole is a versatile compound with significant potential in pharmaceutical, materials science, dye synthesis, and catalysis. Its halogenated indazole structure makes it an essential intermediate for the development of biologically active compounds, as well as functional materials and chemical catalysts, offering advantages in terms of reactivity, stability, and electronic properties.