175278-11-2 | 2-BROMO-4,6-DIFLUOROIODOBENZENE

CAS:175278-11-2 | 2-BROMO-4,6-DIFLUOROIODOBENZENE,Description

Synthesis Analysis

The synthesis of halogenated benzene derivatives, including 1-Bromo-3,5-difluoro-2-iodobenzene, typically involves strategic halogenation and coupling reactions. For instance, the CuI-catalyzed coupling of 1-bromo-2-iodobenzenes with beta-keto esters leads to substituted benzofurans, demonstrating the reactivity of bromo-iodobenzene compounds in domino transformations involving C-C and C-O bond formations (Biao Lu, Bao Wang, Yihua Zhang, D. Ma, 2007).

Molecular Structure Analysis

The molecular structure of 1-Bromo-3,5-difluoro-2-iodobenzene is defined by the presence of bromo, iodo, and fluoro groups attached to the benzene ring. These substituents influence the electronic and steric properties of the molecule. For example, halogen-bonded compounds involving halogenated benzenes exhibit distinct molecular geometries and non-covalent interactions, such as halogen bonds, which are critical in determining their structural characteristics (Jasmine Viger‐Gravel, I. Korobkov, D. L. Bryce, 2015) .

Chemical Reactions and Properties

Halogenated benzene derivatives are versatile reagents in organic synthesis. They participate in various chemical reactions, including coupling reactions, nucleophilic substitutions, and transformations leading to the synthesis of complex organic compounds. The presence of multiple halogens enhances their reactivity and allows for selective functionalization (V. Diemer, F. Leroux, F. Colobert, 2011).

Physical Properties Analysis

The physical properties of 1-Bromo-3,5-difluoro-2-iodobenzene, such as boiling point, melting point, and solubility, are influenced by the halogen substituents. These properties are crucial for its handling and application in organic synthesis. For instance, halogen bonding in crystal structures can affect the melting points and solubility of halogenated compounds (Jasmine Viger‐Gravel, I. Korobkov, D. L. Bryce, 2015) .

Chemical Properties Analysis

The chemical properties of 1-Bromo-3,5-difluoro-2-iodobenzene, such as reactivity and stability, are significantly determined by the nature and position of the halogen substituents on the benzene ring. These properties dictate its utility in organic synthesis, particularly in reactions requiring specific reactivity patterns of halogen atoms (V. Diemer, F. Leroux, F. Colobert, 2011).

Scientific Research Applications

• Synthesis of 4-bromo-2,6-difluorobenzoic acid 
  • Application: 1-Bromo-3,5-difluoro-2-iodobenzene is used as a starting material in the synthesis of 4-bromo-2,6-difluorobenzoic acid. This compound could be used as a building block in the synthesis of more complex organic molecules.
  • Results: The end product of this synthesis is 4-bromo-2,6-difluorobenzoic acid.
• Molecular dynamics simulation and experimental study of 3,5-difluoro-2,4,6-trinitroanisole/2,4,6,8,10,12-hexanitrohexaazaisowurtzitane mixed components 
  • Application: The compound is used in the design of a new melt-cast explosive with high energy and low sensitivity. The casting carrier 3,5-difluoro-2,4,6-trinitroanisole (DFTNAN) and the high-energy component 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (CL-20) were taken as examples to design this new explosive.
  • Method: Molecular dynamics method was used to theoretically study the binding energy, cohesive energy density, radial distribution function, and mechanical properties of DFTNAN/CL-20 systems with different mass ratios.
  • Results: The system with a mass ratio of 40:60 had the highest binding energy and cohesive energy density, indicating that the system had the best stability. The safety performance of the optimized DFTNAN/CL-20 system (40DFTNAN/60CL-20) including mechanical sensitivity and thermal sensitivity was tested experimentally. The results confirm that compared with CL-20, the safety of 40DFTNAN/60 CL-20 was improved on the friction sensitivity decreases by 60%, the impact sensitivity decreases by 8%, and the thermal sensitivity increases from 228.81 to 248.96 °C.

Safety And Hazards

The compound has been classified with the signal word “Warning” and hazard statements H315, H319, H335. Precautionary statements include P261, P305, P338, P351.

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Uses