884495-00-5 | 4-BROMO-5-FLUORO-2-METHOXYPYRIDINE

CAS:884495-00-5 | 4-BROMO-5-FLUORO-2-METHOXYPYRIDINE,Description

4-Bromo-5-fluoro-2-methoxypyridine is a halogenated pyridine derivative that has gained attention due to its potential as a building block in medicinal chemistry. The presence of bromo, fluoro, and methoxy substituents on the pyridine ring makes it a versatile intermediate for various chemical transformations and syntheses of complex organic compounds.

Synthesis Analysis

The synthesis of compounds related to 4-Bromo-5-fluoro-2-methoxypyridine often involves halogenation, methoxylation, and other substitution reactions. For instance, the synthesis of bromido gold(i) complexes with a 2-methoxypyridin-5-yl residue demonstrates the utility of halogenated pyridines in forming compounds with potential biological activity. Another study reports the synthesis of fluoropyridines, which could be related to the fluoro component of 4-Bromo-5-fluoro-2-methoxypyridine, through a fluorodenitration reaction mediated by tetrabutylammonium fluoride under mild conditions. Additionally, the synthesis of 5-bromo-2-methoxy-6-methylaminopyridine-3-carboxylic acid involves a series of reactions including methoxylation and bromination, highlighting the reactivity of bromo and methoxy substituents on the pyridine ring.

Molecular Structure Analysis

The molecular structure of halogenated pyridines is crucial for their reactivity and the type of chemical reactions they can undergo. For example, the synthesis of halogen-rich intermediates for the construction of pentasubstituted pyridines relies on the specific arrangement of halogens on the pyridine ring. The molecular structure, particularly the position of substituents, dictates the reactivity and the possibility of further functionalization of the molecule.

Chemical Reactions Analysis

Chemical reactions involving 4-Bromo-5-fluoro-2-methoxypyridine and related compounds are diverse. The chemoselective functionalization of a related compound, 5-bromo-2-chloro-3-fluoropyridine, shows how different substituents on the pyridine ring can be selectively targeted for substitution reactions. Similarly, the synthesis of methyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate from 5-bromo-2-methoxypyridine involves a lithium-bromine exchange reaction, demonstrating the reactivity of the bromo substituent.

Physical and Chemical Properties Analysis

The physical and chemical properties of 4-Bromo-5-fluoro-2-methoxypyridine are influenced by its substituents. The presence of electron-withdrawing groups such as bromo and fluoro can affect the acidity, basicity, and overall reactivity of the pyridine ring. The methoxy group, being an electron-donating substituent, can also impact the chemical behavior of the compound. These properties are essential for understanding the compound's behavior in various solvents and reaction conditions, as well as its potential interactions with biological targets.

Scientific Research Applications

1. Synthesis of Pyridine Nucleosides

4-Bromo-5-fluoro-2-methoxypyridine has been utilized in the synthesis of pyridine nucleosides related to 5-fluorocytosine and 5-fluorouracil. These nucleosides have significance in medical chemistry, particularly in the creation of compounds that have potential therapeutic uses (Nesnow & Heidelberger, 1975).

2. Intermediate in Synthesis of Complex Compounds

This compound has been employed as an intermediate in the synthesis of more complex compounds. For instance, in the efficient synthesis of 5-bromo-2-methoxy-6-methylaminopyridine-3-carboxylic acid, a component of dopamine D2 and D3 and serotonin-3 (5-HT3) receptors antagonist (Hirokawa, Horikawa, & Kato, 2000).

3. Halogen-rich Intermediate for Medicinal Chemistry

5-Bromo-2-chloro-4-fluoro-3-iodopyridine, a halogen-rich compound synthesized using 4-Bromo-5-fluoro-2-methoxypyridine, serves as a valuable building block in medicinal chemistry research. It facilitates the creation of pentasubstituted pyridines with functionalities for chemical manipulations (Wu et al., 2022).

4. Role in Pyridyne Chemistry

4-Bromo-5-fluoro-2-methoxypyridine has been used in the study of pyridyne chemistry. For example, 3-Bromo-2-chloro-4-methoxypyridine, a related compound, has been developed as a practical 2,3-pyridyne precursor (Walters, Carter, & Banerjee, 1992).

5. Deprotometalation of Substituted Pyridines

In a study involving deprotometalation of substituted pyridines, 4-Bromo-5-fluoro-2-methoxypyridine derivatives were used to understand the regioselectivity and computed CH acidity relationships. This study provided insights into the chemical behavior of methoxy- and fluoro-pyridines (Hedidi et al., 2016).

6. Amination and Functionalization Studies

The compound has been a subject of research in amination and functionalization studies. For example, research on chemoselective amination of related compounds like 5-bromo-2-chloro-3-fluoropyridine helps understand the behavior of these types of compounds under different conditions (Stroup et al., 2007).

Safety And Hazards

4-Bromo-5-fluoro-2-methoxypyridine is considered hazardous. It has been assigned the GHS07 pictogram and the signal word “Warning”. Hazard statements associated with this compound include H302, H315, H319, and H335. Precautionary measures include avoiding dust formation, avoiding breathing mist, gas or vapours, avoiding contact with skin and eye, using personal protective equipment, wearing chemical impermeable gloves, ensuring adequate ventilation, removing all sources of ignition, and evacuating personnel to safe areas.

More Information