134168-97-1 | 3-Fluoro-5-bromoaniline

CAS:134168-97-1 | 3-Fluoro-5-bromoaniline,Description

3-Bromo-5-fluoroaniline is a chemical compound with the molecular formula C6H5BrFN. It has a molecular weight of 190.02 g/mol. This compound is used in the preparation of various pharmaceuticals.

Molecular Structure Analysis

The molecular structure of 3-Bromo-5-fluoroaniline consists of a benzene ring substituted with a bromine atom, a fluorine atom, and an amine group. The IUPAC name for this compound is 3-bromo-5-fluoroaniline.

Scientific Research Applications

Synthesis and Biological Activities

3-Bromo-5-fluoroaniline is a key intermediate in the synthesis of various biologically active compounds. For instance, it has been used in the synthesis of thieno[3,2-c]quinoline and pyrrolo[3,2-c]quinoline derivatives. These compounds have demonstrated significant antibacterial activity against both gram-positive and gram-negative bacterial strains, as well as notable antifungal properties (Abdel‐Wadood et al., 2014) .

Synthetic Methodology Development

Research has also focused on developing new synthetic methodologies involving 3-Bromo-5-fluoroaniline. For example, it was used as a starting material for the synthesis of 1-(4-bromo-2-fluorophenyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one, an important intermediate in the synthesis of many biologically active compounds (Wang et al., 2016).

Versatile Synthesis Applications

Another study focused on the synthesis of 5-bromo-2-fluoro-3-pyridylboronic acid using 3-Bromo-5-fluoroaniline, demonstrating its versatility in the synthesis of 3,5-disubstituted 2-fluoropyridines and 2-pyridones. This highlights the compound's utility in creating a range of substituted pyridines, which are valuable in various chemical and pharmaceutical applications (Sutherland & Gallagher, 2003).

Radioligand Development for Medical Imaging

In medical imaging, 3-Bromo-5-fluoroaniline derivatives have been explored as radioligands. For instance, a study investigated the synthesis of [11C]SP203, a radioligand for imaging brain metabotropic glutamate 5 receptors (mGluR5) in monkey brains using PET scans. This application is significant for neuroscience research and potential clinical applications (Siméon et al., 2012) .

Environmental Applications

In environmental science, the degradation of 3-fluoroaniline by Rhizobium sp. was studied, highlighting the compound's role in biodegradation research. This is relevant for understanding the environmental impact and breakdown of fluoroaniline compounds (Zhao et al., 2019).

Safety And Hazards

3-Bromo-5-fluoroaniline is harmful if swallowed, in contact with skin, or if inhaled. It causes skin irritation and serious eye irritation. It may also cause respiratory irritation.

Future Directions

3-Bromo-5-fluoroaniline is used in the preparation of heterotricyclic carboxamides as RIG-1 agonists for treatment cell proliferation disorders. Its future directions could involve further exploration of its potential uses in pharmaceutical synthesis.

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