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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aniline and substituted anilines

2,6-Difluoro-4-iodoaniline (CAS No. 141743-49-9): A Comprehensive Overview

2,6-Difluoro-4-iodoaniline is a highly specialized organic compound with the CAS registry number 141743-49-9. This compound belongs to the class of aromatic amines, specifically substituted anilines, and is characterized by its unique substitution pattern on the benzene ring. The presence of two fluorine atoms at the 2 and 6 positions and an iodine atom at the 4 position imparts distinctive chemical properties, making it a valuable molecule in various research and industrial applications.

The molecular formula of 2,6-difluoro-4-iodoaniline is C6H3F2IN, with a molecular weight of approximately 305.9 g/mol. Its structure consists of a benzene ring with three substituents: two fluorine atoms at the ortho positions (positions 2 and 6) and an iodine atom at the para position (position 4). The amino group (-NH2) is directly attached to the benzene ring at position 1. This substitution pattern not only influences the compound's physical properties but also plays a crucial role in its reactivity and potential applications.

One of the key features of 2,6-difluoro-4-iodoaniline is its high stability due to the electron-withdrawing effects of the fluorine atoms and the iodine atom. These substituents deactivate the benzene ring towards electrophilic aromatic substitution reactions but enhance its reactivity in certain nucleophilic or radical-based reactions. This makes it a versatile building block in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and advanced materials.

Recent studies have highlighted the potential of 2,6-difluoro-4-iodoaniline as an intermediate in the synthesis of bioactive compounds. For instance, researchers have utilized this compound to develop novel anti-inflammatory agents by incorporating it into heterocyclic frameworks. The iodine atom at position 4 serves as an excellent leaving group, enabling nucleophilic substitutions that can introduce diverse functional groups into the molecule.

In addition to its role as an intermediate, 2,6-difluoro-4-iodoaniline has been explored for its applications in materials science. Its ability to form stable radicals under certain conditions has led to investigations into its use in polymerization processes and as a precursor for conducting polymers. These findings underscore its versatility across multiple disciplines.

The synthesis of 2,6-difluoro-4-iodoaniline typically involves multi-step processes that require precise control over reaction conditions. One common approach involves the electrophilic substitution of aniline derivatives with fluorine and iodine substituents. Recent advancements in catalytic methods have improved the efficiency and selectivity of these reactions, making large-scale production more feasible.

From a toxicological perspective, understanding the safety profile of 2,6-difluoro-4-iodoaniline is critical for its industrial use. Preliminary studies indicate that it exhibits low acute toxicity; however, long-term exposure effects require further investigation. Regulatory agencies are increasingly emphasizing comprehensive safety assessments for such compounds to ensure their safe handling and use in various applications.

In conclusion, 2,6-difluoro-4-iodoaniline (CAS No. 141743-49-9) stands out as a significant molecule with diverse applications across chemistry and materials science. Its unique substitution pattern offers opportunities for innovative research and development while posing challenges related to synthesis optimization and safety evaluation.

• 923294-24-0(Benzenamine, 2,4,6-trifluoro-3,5-diiodo-)
• 1991-43-1(Benzenamine, 2,3,5,6-tetrafluoro-4-iodo-)
• 61272-76-2(4-Fluoro-2-iodoaniline)
• 582319-15-1(2,4-Difluoro-6-iodoaniline)
• 886362-82-9(2-Fluoro-5-iodoaniline)
• 660-49-1(3-Fluoro-5-iodoaniline)
• 29632-74-4(2-Fluoro-4-iodoaniline)
• 923294-22-8(Benzenamine, 2,3,4,6-tetrafluoro-5-iodo-)
• 886762-73-8(2-Fluoro-6-iodoaniline)
• 1301739-25-2(2-Fluoro-4,6-diiodoaniline)