65896-11-9 | 2-BROMO-6-FLUOROANILINE

CAS:65896-11-9 | 2-BROMO-6-FLUOROANILINE,Description

2-Bromo-6-fluoroaniline is a compound that has been the subject of various research studies due to its utility in the synthesis of other chemical compounds and its potential applications in medical and material sciences. The compound is characterized by the presence of a bromine atom at the second position and a fluorine atom at the sixth position on the aniline ring, which is a derivative of benzene with an amine group attached to it.

Synthesis Analysis

The synthesis of derivatives of 2-bromo-6-fluoroaniline has been explored in several studies. For instance, 2-bromo-6-isocyanopyridine has been identified as an optimal reagent for multicomponent chemistry due to its stability and synthetic efficiency, and it has been used in the efficient synthesis of potent opioids like carfentanil. Additionally, 2-bromo-6-[(18) F]fluoropyridine has been prepared using transition metal-mediated chemistry, demonstrating its potential as a synthon for constructing fluorine-18-labelled molecules. Furthermore, 2-bromo-6-fluorotoluene, an important medical intermediate, has been prepared from 2-amino-6-nitrotoluene through a series of reactions including Gattermann diazonium salt substitution, reduction, and Schiemann reaction.

Molecular Structure Analysis

The molecular structure of related compounds such as 2,6-dibromo-3-chloro-4-fluoroaniline has been determined, revealing classical intra- and intermolecular hydrogen bonds and dispersive halogen interactions within the crystal structure. These structural features are crucial for understanding the reactivity and potential applications of these compounds.

Chemical Reactions Analysis

2-Bromo-6-fluoroaniline and its derivatives participate in various chemical reactions. For example, the radiosynthesis of 2-amino-5-[18F]fluoropyridines has been achieved by palladium-catalyzed amination of 2-bromo-5-[18F]fluoropyridine with different amines. SNAr displacements with 6-halopurine nucleosides have been studied, showing the reactivity order of halogens in these reactions. These studies provide insights into the reactivity patterns of halogenated anilines and their potential in synthetic chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-bromo-6-fluoroaniline derivatives are influenced by the presence of halogen atoms, which can affect their boiling points, melting points, solubility, and stability. The synthesis and characterization of 2,6-dialkyl-4-bromoaniline, for example, involved controlling reaction conditions to optimize yield and purity, indicating the importance of understanding these properties for successful synthesis. The crystal structure of related compounds provides additional information on the solid-state properties, such as lattice parameters and molecular packing.

Scientific Research Applications

• Medical Intermediate Synthesis :
  • 2-Bromo-6-fluorotoluene, a derivative of 2-Bromo-6-fluoroaniline, is noted as an important medical intermediate. It is prepared from 2-Amino-6-nitrotoluene through a series of reactions, including Gattermann diazonium salt substitution, reduction, and Schiemann reaction (Li Jiang-he, 2010).
• Antimalarial Activity :
  • A study on dihydroartemisinin derivatives containing bromo, heterocyclic, or aromatic amine functions, including compounds related to 2-Bromo-6-fluoroaniline, showed effectiveness against Plasmodium falciparum. These compounds demonstrated more efficacy against certain clones and were not cross-resistant with existing antimalarials (A. Lin et al., 1990).
• Biological Activities against Pathogenic Strains :
  • Research on thieno[3,2‐c]quinoline and pyrrolo[3,2‐c]quinoline derivatives, which utilize 2‐Bromo‐4‐fluoroaniline, indicated significant antibacterial activity against various gram-positive and gram-negative bacterial strains. Some compounds also displayed remarkable antifungal activity (F. K. Abdel‐Wadood et al., 2014) .
• Key Intermediate in Pharmaceutical Synthesis :
  • 2-Fluoro-4-bromobiphenyl, a key intermediate for manufacturing flurbiprofen (a non-steroidal anti-inflammatory and analgesic material), is synthesized using 2-fluoro-4-bromoaniline. The synthesis methods reviewed highlight its importance in pharmaceutical manufacturing (Yanan Qiu et al., 2009).
• Synthesis of Bioactive Compounds :
  • The synthesis of 1-(4-bromo-2-fluorophenyl)-1,3-dihydro-2H-imidazo[4,5-c] pyridin-2-one, an important intermediate for various biologically active compounds, demonstrates the versatility of 2-fluoro-4-bromoaniline as a starting material for synthesizing complex structures (Linxiao Wang et al., 2016).

Safety And Hazards

2-Bromo-6-fluoroaniline is considered hazardous. It may cause skin irritation, serious eye irritation, and respiratory irritation. It is harmful if swallowed, in contact with skin, or if inhaled. It should be handled with care, using personal protective equipment and in a well-ventilated area.

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