630125-49-4 | 3-BROMO-5-NITROBENZOTRIFLUORIDE

CAS:630125-49-4 | 3-BROMO-5-NITROBENZOTRIFLUORIDE,Description

Synthesis Analysis

The synthesis of bromo-nitro compounds typically involves the introduction of bromo and nitro groups into an aromatic system. For instance, the synthesis of tris(5-bromo-2-methoxyphenyl)antimony bis(2-nitrobenzoate) was achieved by reacting tris(5-bromo-2-methoxyphenyl)antimony with 2-nitrobenzoic acid in the presence of hydrogen peroxide. Similarly, 3-bromo substituted flavones were synthesized from 2-hydroxy-3,5-dibromo-4'nitro dibenzoyl methane by dissolving it in dimethylformamide (DMF) and adding bromine, followed by crystallization. These methods suggest that the synthesis of 3-Bromo-5-nitrobenzotrifluoride could potentially be carried out through halogenation and nitration reactions under controlled conditions.

Molecular Structure Analysis

The molecular structure of bromo-nitro aromatic compounds can be complex, with the potential for intramolecular interactions. For example, in the structure of tris(5-bromo-2-methoxyphenyl)antimony bis(2-nitrobenzoate), the antimony atom exhibits distorted trigonal bipyramidal coordination, with specific intramolecular contacts between antimony and oxygen atoms. These structural features are crucial as they can influence the reactivity and physical properties of the compound.

Chemical Reactions Analysis

The reactivity of bromo-nitro compounds with nucleophiles has been studied, revealing interesting substitution and rearrangement reactions. 3-Bromo-2-nitrobenzo[b]thiophene, for example, reacts with amines to give both expected and unexpected substitution products, indicating a complex reaction mechanism that involves anionic intermediates and nitro group migration. These findings suggest that 3-Bromo-5-nitrobenzotrifluoride could also exhibit unique reactivity patterns with nucleophiles, potentially leading to novel compounds.

Physical and Chemical Properties Analysis

The physical and chemical properties of bromo-nitro aromatic compounds are influenced by their molecular structure. The presence of bromo and nitro groups can affect the electron density and polarity of the molecule, which in turn can impact its boiling point, melting point, solubility, and reactivity. For instance, the melting points of newly synthesized 3-bromo flavones were determined using capillary tube methods. The crystal packing and hydrogen bonding patterns observed in the structures of related compounds also suggest that 3-Bromo-5-nitrobenzotrifluoride could have distinct solid-state properties.

Scientific Research Applications

1. Bromine Stability in Derivatives

The bromine atom in compounds like 3-Bromo-5-nitrobenzotrifluoride is not labile in various derivatives. This stability is observed in compounds like 5-bromo-1-ethylbenzimidazole, its nitro derivatives, and related benzimidazolium salts (Yu. P. Andreichikov & A. Simonov, 1970).

2. Synthesis Applications

3-Bromo-5-nitrobenzotrifluoride is used in synthesis processes, like the continuous-flow millireactor system for producing 5-fluoro-2-nitrobenzotrifluoride. This process emphasizes safety and efficiency, offering enhanced control and process efficiency compared to traditional methods (Peng Chen et al., 2020).

3. Reactivity with Amines

The compound reacts with amines in specific conditions, leading to novel aromatic nucleophilic substitutions and rearrangements. This reaction is significant for synthesizing certain derivatives (F. Guerrera et al., 1995).

4. Mobility in Reactions

The relative mobility of the nitro group and fluorine atom in derivatives of 3-Bromo-5-nitrobenzotrifluoride can be studied to understand reaction mechanisms. Such studies aid in the synthesis and manipulation of these compounds (I. A. Khalfina & V. M. Vlasov, 2002).

5. Synthesis of Polyimides

It is instrumental in the synthesis of new diamine monomers containing both benzimidazole rings and trifluoromethyl groups. These monomers lead to polyimides with high thermal stability, solubility in polar solvents, and desirable physical properties, crucial for various industrial applications (Hyungsam Choi et al., 2008).

6. Photochemically Active Reagents

Derivatives of 3-Bromo-5-nitrobenzotrifluoride can be used to create photochemically active bifunctional reagents. These reagents have potential applications in biochemistry, particularly in the cross-linking of biopolymers (F. Seela, 1976).

Safety And Hazards

3-Bromo-5-nitrobenzotrifluoride is harmful if swallowed, in contact with skin, or if inhaled. It causes skin irritation and serious eye irritation. It is a combustible liquid.

Future Directions

The application of 3-Bromo-5-nitrobenzotrifluoride is diverse and expanding. It is used in the synthesis of fluorinated pharmaceuticals, such as anti-HIV drugs, anti-inflammatory drugs, and anticancer drugs.

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