1009-22-9 | 2'-Bromo-4'-fluoroacetanilide

CAS:1009-22-9 | 2'-Bromo-4'-fluoroacetanilide,Description

N-(2-bromo-4-fluorophenyl)acetamide is a chemical compound that has been the subject of various studies due to its potential applications in the medical and pharmaceutical fields. While the provided papers do not directly discuss N-(2-bromo-4-fluorophenyl)acetamide, they do provide insights into similar compounds, which can be used to infer certain properties and behaviors of the compound .

Synthesis Analysis

The synthesis of related acetamide compounds typically involves reactions such as alkylation, nitration, and the use of reagents like POCl3 in acetate. For example, N-[4-(4-Bromobutoxy)-2-nitrophenyl]acetamide was synthesized from p-acetamidophenol via alkylation and nitration, suggesting that similar methods could potentially be applied to synthesize N-(2-bromo-4-fluorophenyl)acetamide.

Molecular Structure Analysis

The molecular structure of acetamide derivatives is often characterized by the dihedral angles between the phenyl ring and the acetamide group, as well as the interactions between different functional groups. For instance, in 2-(4-Bromophenyl)-N-(2-methoxyphenyl)acetamide, the dihedral angle between the two benzene rings is significant, and intermolecular hydrogen bonds and contacts form chains in the crystal structure. These structural features are crucial for understanding the physical properties and reactivity of the compound.

Chemical Reactions Analysis

Acetamide compounds can participate in various chemical reactions, including hydrogen bonding and interactions with other molecules. For example, 2,2-Dibromo-N-(4-fluorophenyl)acetamide forms chains in the crystal structure through C-H⋯O and N-H⋯O hydrogen bonding. These interactions are important for the stability and reactivity of the molecules.

Physical and Chemical Properties Analysis

The physical and chemical properties of acetamide derivatives can be deduced from spectroscopic data and computational studies. For instance, vibrational spectroscopy and quantum computations have been used to assign vibrational modes and investigate the stability of molecules like 5-[(4-Bromophenyl)acetamido]-2-(4-tert-butylphenyl) benzoxazole. The HOMO-LUMO analysis and NBO analysis provide insights into charge transfer and hyper-conjugative interactions within the molecule. These analyses are essential for predicting the behavior of N-(2-bromo-4-fluorophenyl)acetamide in various environments.

Scientific Research Applications

• Several derivatives of N-aryl-2,4-dichlorophenoxyacetamide, including compounds related to N-(2-bromo-4-fluorophenyl)acetamide, have been characterized for potential use as pesticides. These derivatives have been studied using X-ray powder diffraction techniques (Olszewska, Pikus, & Tarasiuk, 2008).
• Derivatives of N-substituted phenylacetamide, including compounds similar to N-(2-bromo-4-fluorophenyl)acetamide, have been synthesized and evaluated for anticonvulsant and antidepressant activities. Some of these compounds showed significant effectiveness in reducing immobility times in mice and protecting against seizures (Xie, Tang, Pan, & Guan, 2013).
• A study explored the synthesis and antimicrobial activity of sulfide and sulfone derivatives of compounds including 4-(2-chloro-4-fluorophenyl)-1,3-thiazol-2-amine/acetamide. The synthesized compounds demonstrated antimicrobial activity against various bacterial and fungal strains (Badiger, Mulla, Khazi, & Khazi, 2013).
• A microwave-assisted synthesis was performed for 2-(2-acetamidophenyl)-2-oxo-N phenyl acetamide and related derivatives. Some of these compounds exhibited high inhibitory effects against Aspergillus niger and Staphylococcus aureus (Ghazzali, El‐Faham, Abdel-Megeed, & Al-farhan, 2012).
• N-[4-[(4-fluorophenyl)sulfonyl]phenyl] acetamide (CL 259,763), a related compound, was identified as an orally active compound that can modify lymphoid cell populations affected by tumor growth. It showed potential in enhancing the immune response to tumors (Wang, Ruszala-Mallon, Wallace, Citarella, Lin, & Durr, 2004).
• Leuckart synthesis of acetamide derivatives, including compounds related to N-(2-bromo-4-fluorophenyl)acetamide, was conducted to explore their potential as cytotoxic, anti-inflammatory, analgesic, and antipyretic agents. Certain compounds exhibited activities comparable to standard drugs (Rani, Pal, Hegde, & Hashim, 2016).
• N-(2-Hydroxyphenyl)acetamide, a similar compound, was studied as an intermediate for the natural synthesis of antimalarial drugs. Its chemoselective monoacetylation was researched, highlighting its potential application in drug synthesis (Magadum & Yadav, 2018).

Safety And Hazards

“N-(2-bromo-4-fluorophenyl)acetamide” should be handled with care. Avoid breathing its dust, fume, gas, mist, vapors, or spray. Avoid contact with skin and eyes. Use personal protective equipment and ensure adequate ventilation. Remove all sources of ignition and evacuate personnel to safe areas.

Future Directions

“N-(2-bromo-4-fluorophenyl)acetamide” is mainly used as an intermediate in organic synthesis reactions. It can be used to prepare other organic compounds, such as drugs and dyes. Future research could explore new synthesis methods, potential applications, and safety measures for this compound.

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