88149-49-9 | 2,6-Dibromo-4-(trifluoromethoxy)aniline

CAS:88149-49-9 | 2,6-Dibromo-4-(trifluoromethoxy)aniline,Description

Synthesis Analysis 2,6-Dibromo-4-(trifluoromethoxy)aniline, an important agrochemical intermediate, is synthesized from 4-trifluoromethoxy aniline. The optimal synthesis conditions involve brominating agents Br2 and Br2-H2O2, with a molar ratio of Br2 to 4-trifluoromethoxy aniline at 1:1, using methylene dichloride-water as the solvent and under reflux conditions. This process yields a product with over 97% yield and purity above 99.5% (Ding Zhi-yuan, 2011).

Molecular Structure Analysis The trifluoromethoxy group's structural role in aniline derivatives significantly impacts their chemical properties and reactivity. For example, in organometallic complexes like η6-(4-(trifluoromethoxy)aniline)tricarbonylchromium, the trifluoromethoxy group is nearly perpendicular to the arene ring, indicating distinct conformational preferences due to the trifluoromethoxy substituent (F. Rose-munch et al., 1994).

Chemical Reactions and Properties Trifluoromethoxy-substituted anilines exhibit unique reactivity, such as undergoing metalation with organolithium reagents, enabling diverse structural elaboration. The metalation process shows optional site selectivity, which is significantly influenced by the N-protective group employed, demonstrating the intricate chemical behavior of trifluoromethoxy-substituted anilines (F. Leroux, E. Castagnetti, M. Schlosser, 2003).

Physical Properties Analysis The physical properties, such as dipole moments and tendencies for intermolecular hydrogen bonding, are crucial in understanding the behavior of compounds like 2,6-Dibromo-4-(trifluoromethoxy)aniline. For instance, the analysis of dipole moments in related compounds helps in assessing their chemical reactivity and interaction capabilities, showcasing the significant role of the trifluoromethoxy group (D. E. Grocock et al., 1971).

Chemical Properties Analysis The introduction of the trifluoromethoxy group significantly impacts the chemical properties of aniline derivatives. This effect can be observed in the synthesis and reactivity of compounds, where the trifluoromethoxy group often enhances their utility in various applications, such as in agrochemicals. The specific synthesis methods and the resultant properties highlight the chemical versatility and significance of the 2,6-Dibromo-4-(trifluoromethoxy)aniline compound in scientific research and applications (Zhou Li-shan, 2002).

Scientific Research Applications

• Synthesis of New Benzodiazepines : Trifluoromethoxy-substituted anilines like 2,6-Dibromo-4-(trifluoromethoxy)aniline undergo hydrogen/lithium permutation (metalation), which can be key in synthesizing new benzodiazepines through organometallic reagents (Leroux, Castagnetti, & Schlosser, 2003).
• Discovery of Pharmaceuticals and Functional Materials : A protocol involving ortho-trifluoromethoxylated aniline derivatives aids in the discovery and development of new pharmaceuticals, agrochemicals, and functional materials (Feng & Ngai, 2016).
• Agrochemical Intermediate : 2,6-Dichloro-4-trifluoromethyl aniline, closely related to 2,6-Dibromo-4-(trifluoromethoxy)aniline, serves as an intermediate for efficient, low toxic pesticides and herbicides (Zhou Li-shan, 2002).
• High-Yield Synthesis Process : An improved synthesis process of 2,6-dibromo-4-trifluoromethoxy aniline, significant for agrochemicals, yields a high reaction yield and purity (Ding Zhi-yuan, 2011).
• Energy Conversion in Solar Cells : Novel polymers based on derivatives of aniline improve energy conversion efficiency in dye-sensitized solar cells (Shahhosseini et al., 2016).
• Fungicidal Activities : N-(2,6-dibromo-4-(trifluoromethoxy)phenyl)-2-methoxy-4-(trifluoromethyl)thiazol-5-ylcarboxamide exhibits potent fungicidal activities against Rhizoctonia solani (Liu et al., 2017).
• Insecticide Synthesis : The compound is used in the synthesis of Novaluron, a novel insecticide, with significant yield and purity (Wen Zi-qiang, 2008).

Safety And Hazards

2,6-Dibromo-4-(trifluoromethoxy)aniline is harmful if swallowed or inhaled. It causes skin irritation, serious eye irritation, and may cause respiratory irritation. Personal protective equipment and face protection should be worn when handling this chemical. It should not be allowed to come into contact with the skin, eyes, or clothing. It should only be used under a chemical fume hood, and inhalation or ingestion should be avoided.

Future Directions

2,6-Dibromo-4-(trifluoromethoxy)aniline is used in the synthesis of novel pyridylpyrazole acid derivatives, which are used in the preparation of agricultural insecticides. This suggests potential future directions in the development of new insecticides.

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