261945-75-9 | 1-bromo-2,5-difluoro-4-(trifluoromethyl)benzene

CAS:261945-75-9 | 1-bromo-2,5-difluoro-4-(trifluoromethyl)benzene,Description

The compound 1-Bromo-2,5-difluoro-4-(trifluoromethyl)benzene is a halogenated aromatic molecule that contains bromine and fluorine substituents on a benzene ring. The presence of these halogens suggests that it could be a versatile intermediate in organic synthesis, particularly in the formation of organometallic compounds, as halogens are good leaving groups in such reactions .

Synthesis Analysis

The synthesis of halogenated benzene derivatives often involves palladium-catalyzed cross-coupling reactions, as seen in the preparation of various ethynylferrocene compounds from 1,3,5-tribromobenzene . Similarly, 1-Bromo-3,5-bis(trifluoromethyl)benzene, a closely related compound, is synthesized from 1,3-bis(fluoromethyl)benzene using N,N'-dibromo-5,5-dimethylhydantoin in acidic media . This method could potentially be adapted for the synthesis of 1-Bromo-2,5-difluoro-4-(trifluoromethyl)benzene by altering the substitution pattern on the starting material.

Molecular Structure Analysis

The molecular structure of halogenated benzene derivatives is often characterized using X-ray crystallography. For instance, the crystal structures of various brominated benzene compounds have been determined, revealing interactions such as C–H···Br, C–Br···Br, and C–Br···π, which could influence the reactivity and properties of these molecules . These structural insights are crucial for understanding the reactivity of 1-Bromo-2,5-difluoro-4-(trifluoromethyl)benzene.

Chemical Reactions Analysis

Halogenated benzenes are known to participate in various chemical reactions. For example, 1-bromo-4-(3,7-dimethyloctyl)benzene is used as a precursor for the synthesis of graphene nanoribbons . The presence of bromine in 1-Bromo-2,5-difluoro-4-(trifluoromethyl)benzene suggests that it could undergo similar nucleophilic substitutions or serve as a building block for more complex structures. Additionally, the compound could be involved in electrophilic aromatic substitution reactions due to the electron-withdrawing effect of the fluorine atoms.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated benzenes are influenced by the nature and position of the substituents. For example, the fluorescence properties of 1-Bromo-4-(2,2-diphenylvinyl)benzene have been studied, showing significant differences in fluorescence intensity between the solution and solid states . This indicates that the physical state can greatly affect the properties of such compounds. The presence of both bromine and fluorine in 1-Bromo-2,5-difluoro-4-(trifluoromethyl)benzene would likely result in unique physical and chemical properties, such as boiling point, density, and reactivity, which could be explored through experimental studies.

Scientific Research Applications

Application in Agrochemical and Pharmaceutical Industries

• Summary of the Application: Trifluoromethylpyridine (TFMP) derivatives, which include 1-Bromo-2,5-difluoro-4-(trifluoromethyl)benzene, are used in the agrochemical and pharmaceutical industries. The major use of TFMP derivatives is in the protection of crops from pests . Several TFMP derivatives are also used in the pharmaceutical and veterinary industries .
• Methods of Application or Experimental Procedures: The synthesis and applications of trifluoromethylpyridine (TFMP) and its derivatives involve various chemical reactions. For example, 2,3-dichloro-5-(trifluoromethyl)-pyridine (2,3,5-DCTF), which is used as a chemical intermediate for the synthesis of several crop-protection products, is in high demand .
• Results or Outcomes: Fluazifop-butyl was the first TFMP derivative introduced to the agrochemical market, and since then, more than 20 new TFMP-containing agrochemicals have acquired ISO common names . Five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials .

Synthesis of Unsymmetrical and Highly Functionalized Carbazoles and Dibenzofurans

• Summary of the Application: This compound is used in the Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes .
• Methods of Application or Experimental Procedures: The exact experimental procedures would be detailed in the respective research papers or patents. Generally, the process involves a Lewis acid-promoted reaction with biaryl triazenes .
• Results or Outcomes: The outcome of this process is the production of unsymmetrical and highly functionalized carbazoles and dibenzofurans .

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