5-Bromo-4-fluoro-1H-indazole
[CAS# 1082041-85-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indazoles
• Name: 5-Bromo-4-fluoro-1H-indazole
• Molecular Formula: C₇H₄BrFN₂
• Molecular Weight: 215.02
• CAS Registry Number: 1082041-85-7
• EC Number: 813-682-7
• SMILES: C1=CC(=C(C2=C1NN=C2)F)Br

Properties

• Solubility: Very slightly soluble (0.28 g/L) (25 °C), Calc.^*
• Density: 1.861±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 332.2±22.0 °C 760 mmHg (Calc.)^*
• Flash point: 154.7±22.3 °C (Calc.)^*
• Index of refraction: 1.693 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+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
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

5-Bromo-4-fluoro-1H-indazole is an organic compound with the molecular formula C7H4BrFN. It belongs to the class of heterocyclic aromatic compounds known as indazoles, which consist of a fused ring structure containing both a benzene ring and a pyrazole ring. This particular indazole derivative contains two halogen atoms: bromine at the 5-position and fluorine at the 4-position of the benzene ring. The presence of these halogens gives the compound unique chemical and physical properties that make it valuable in synthetic chemistry and various applications.

The synthesis of 5-bromo-4-fluoro-1H-indazole typically involves the functionalization of indazole or a closely related precursor compound. One common synthetic route is halogenation of an appropriate indazole derivative using bromine and fluorine-containing reagents under controlled conditions to ensure selective substitution at the desired positions. This results in the introduction of bromine at the 5-position and fluorine at the 4-position of the aromatic ring, yielding the target compound. Other methods, such as nucleophilic substitution reactions or coupling reactions, can also be used to synthesize this halogenated indazole derivative.

The functionalization of the indazole ring with halogen atoms, such as bromine and fluorine, often enhances the compound's reactivity, making it suitable for further chemical transformations. The bromine atom is electrophilic and can participate in nucleophilic substitution reactions, while the fluorine atom, due to its electronegativity, can alter the electronic properties of the molecule. This modification can influence the compound's behavior in various reactions and its interaction with other molecules.

5-Bromo-4-fluoro-1H-indazole and its derivatives are of significant interest in medicinal chemistry, particularly in the development of bioactive compounds. The presence of both a fluorine and bromine atom can enhance the compound's pharmacological properties by modifying its solubility, stability, and ability to interact with biological targets. Indazole derivatives, in general, have been shown to exhibit a variety of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties, making them valuable in the design of new therapeutic agents.

For example, compounds with a similar structure to 5-bromo-4-fluoro-1H-indazole have been studied for their potential to inhibit enzymes involved in cancer progression or inflammation. The halogen substitution can increase the lipophilicity of the compound, allowing it to better cross biological membranes and interact with intracellular targets. Additionally, the halogenated indazoles may exhibit specific interactions with receptors or enzymes, making them useful in drug discovery efforts aimed at treating diseases such as cancer, neurodegenerative disorders, or inflammatory diseases.

In addition to its potential therapeutic applications, 5-bromo-4-fluoro-1H-indazole can also be used as an intermediate in the synthesis of other complex organic compounds. Its reactivity allows it to undergo various reactions, such as nucleophilic substitutions, coupling reactions, and cross-coupling reactions. These reactions enable the creation of diverse functionalized molecules that can be used in materials science, including the development of organic electronics, sensors, and other advanced materials.

Due to the presence of halogen atoms, 5-bromo-4-fluoro-1H-indazole may also exhibit unique electronic and optical properties that can be exploited in the design of new materials for electronic devices. For example, halogenated indazole derivatives have been studied for their use in organic semiconductors, light-emitting diodes (LEDs), and solar cells. The incorporation of halogens can modify the electronic structure of the molecule, influencing its absorption and emission properties, making it suitable for optoelectronic applications.

Like other halogenated organic compounds, 5-bromo-4-fluoro-1H-indazole must be handled with caution. Bromine and fluorine are highly reactive elements, and proper safety protocols should be followed when working with this compound to avoid exposure. It is essential to wear appropriate protective gear, such as gloves, goggles, and lab coats, and to work in a well-ventilated area to minimize the risk of inhaling harmful vapors or coming into direct contact with the substance.

In summary, 5-bromo-4-fluoro-1H-indazole is a halogenated indazole derivative with potential applications in medicinal chemistry, materials science, and organic synthesis. Its reactivity, due to the presence of bromine and fluorine atoms, makes it a valuable intermediate in the development of bioactive compounds and functionalized materials. By exploiting its chemical properties, researchers can design new molecules with specific biological activities or enhance the performance of materials for electronic and optoelectronic applications.