General Description

4-Fluoro-2-Methoxy-5-nitroaniline is a solid compound with a molecular formula of C7H7FN2O3 and a molecular weight of 186.14 g/mol. It has unique properties, such as being sparingly soluble in water but dissolving well in organic solvents. It exhibits aromatic behavior and can undergo various reactions, making it valuable in organic synthesis and medicinal chemistry. Its application lies in its role as a key intermediate in the synthesis of Mereletinib, a potent inhibitor of mutant BRAFV600E kinase used in cancer treatment. However, caution must be taken when handling 4-Fluoro-2-Methoxy-5-nitroaniline due to its toxicity. Proper safety measures, including personal protective equipment and appropriate storage, are necessary to mitigate potential risks.

Figure 1. 4-Fluoro-2-Methoxy-5-nitroaniline

Properties

4-Fluoro-2-Methoxy-5-nitroaniline is a chemical compound with distinct properties. Firstly, it has a molecular formula of C7H7FN2O3 and a molecular weight of 186.14 g/mol. Its structure consists of a benzene ring with a fluorine atom attached at the fourth position, a methoxy group at the second position, and a nitro group at the fifth position. 4-Fluoro-2-Methoxy-5-nitroaniline is a solid compound with a white color. It is sparingly soluble in water but dissolves well in organic solvents like ethanol and acetone. In terms of its chemical reactivity, 4-Fluoro-2-Methoxy-5-nitroaniline exhibits aromatic behavior due to the presence of the benzene ring. It can undergo various types of reactions, including substitution and reduction reactions. Moreover, 4-Fluoro-2-Methoxy-5-nitroaniline possesses both electron-donating and electron-withdrawing groups, which make it a versatile compound for applications in organic synthesis and medicinal chemistry. These properties allow FMNA to be used as an intermediate in the synthesis of pharmaceutical compounds. In conclusion, 4-Fluoro-2-Methoxy-5-nitroaniline is a solid compound with unique properties, making it valuable in various chemical applications, while also requiring careful handling due to its toxicity. ¹

Applications

4-Fluoro-2-Methoxy-5-nitroaniline plays a crucial role in the synthesis of Mereletinib, a potent inhibitor of mutant BRAFV600E kinase that is being developed for the treatment of various cancers. In the process of preparing Mereletinib, 4-Fluoro-2-Methoxy-5-nitroaniline serves as a key intermediate compound. Firstly, 4-Fluoro-2-Methoxy-5-nitroaniline undergoes a series of chemical reactions to introduce specific functional groups, enabling the subsequent formation of the desired molecular structure. Through carefully controlled reactions, the nitro group on 4-Fluoro-2-Methoxy-5-nitroaniline is selectively modified to yield the necessary chemical scaffold for the synthesis of Mereletinib. Subsequently, further chemical transformations are carried out to complete the synthesis of Mereletinib from the intermediate formed by 4-Fluoro-2-Methoxy-5-nitroaniline. The precise manipulation of 4-Fluoro-2-Methoxy-5-nitroaniline in these synthetic steps is critical to ensure the high purity and yield of the final Mereletinib product, highlighting the vital role of 4-Fluoro-2-Methoxy-5-nitroaniline in the preparation of this promising pharmaceutical compound. ²

Safety

4-Fluoro-2-Methoxy-5-nitroaniline is an organic compound widely used in various industries. When discussing the safety aspects of 4-Fluoro-2-Methoxy-5-nitroaniline, it is essential to consider its potential hazards and recommended precautions. 4-Fluoro-2-Methoxy-5-nitroaniline may pose health risks if mishandled or improperly used. It is important to avoid inhalation, ingestion, or skin and eye contact with 4-Fluoro-2-Methoxy-5-nitroaniline, as it can cause irritation and allergic reactions. Prolonged or repeated exposure to 4-Fluoro-2-Methoxy-5-nitroaniline may have harmful effects on the respiratory system, liver, and kidneys. Therefore, it is crucial to work with 4-Fluoro-2-Methoxy-5-nitroaniline in well-ventilated areas and wear appropriate personal protective equipment, including gloves, goggles, and a lab coat. To ensure safe storage and handling of 4-Fluoro-2-Methoxy-5-nitroaniline, it should be stored in a cool, dry, and well-ventilated area away from sources of heat, flames, and incompatible chemicals. It is important to follow proper waste disposal procedures to prevent environmental contamination. In case of accidental exposure or ingestion, immediate medical attention should be sought. It is recommended to familiarize oneself with the Material Safety Data Sheet (MSDS) for 4-Fluoro-2-Methoxy-5-nitroaniline and strictly adhere to the guidelines provided by the manufacturer or regulatory authorities. Overall, ensuring the safety of 4-Fluoro-2-Methoxy-5-nitroaniline requires appropriate handling, storage, and precautionary measures to mitigate potential risks associated with its use. ³

Reference

1. PubChem. COMPOUND SUMMARY: 4-Fluoro-2-methoxy-5-nitroaniline. National Library of Medicine, PubChem CID: 57429072.

2. An EGFR kinase inhibitor and its application in the preparation of anticancer drugs. National Center for Biotechnology Information, 2023, PubChem Patent Summary for CN-111909101-B.

3. 4-Fluoro-2-methoxy-5-nitroaniline. European Chemicals Agency, EC / List no. 806-172-0.