958458-89-4 | 1-Bromo-2-fluoro-3-iodobenzene

CAS:958458-89-4 | 1-Bromo-2-fluoro-3-iodobenzene,Description

1-Bromo-2-fluoro-3-iodobenzene is a halogenated aromatic compound that has not been directly studied in the provided papers. However, its structural analogs, such as 1-bromo-2-iodobenzenes and 1-bromo-2-fluorobenzenes, have been utilized in various chemical syntheses and transformations. These compounds serve as intermediates in the preparation of more complex molecules, including benzofurans, benzothioamides, and heterocyclic compounds.

Synthesis Analysis

The synthesis of halogenated benzene derivatives often involves catalytic processes or halogen exchange reactions. For instance, 1-bromo-2-iodobenzenes can be coupled with beta-keto esters in the presence of a CuI catalyst to form 2,3-disubstituted benzofurans. Similarly, 1-bromo-2-fluorobenzenes can be synthesized from bromodeboronation reactions of aryl boronic acids, demonstrating the versatility of halogenated benzenes in organic synthesis. These methods could potentially be adapted for the synthesis of 1-bromo-2-fluoro-3-iodobenzene.

Molecular Structure Analysis

The molecular structure of halogenated benzenes is significantly influenced by the presence of halogen atoms. Studies using spectroscopic techniques such as FT-IR, FT-Raman, and NMR have provided insights into the vibrational frequencies, molecular geometry, and electronic properties of these compounds. The electronic structure, including HOMO and LUMO energies, indicates that charge transfer occurs within the molecule, which can affect its reactivity.

Chemical Reactions Analysis

Halogenated benzenes participate in various chemical reactions, including nucleophilic aromatic substitution, which is a common method for introducing radioisotopes such as fluorine-18 into aromatic rings. Palladium-catalyzed carbonylative reactions of 1-bromo-2-fluorobenzenes with different nucleophiles have been shown to yield six-membered heterocycles. These reactions highlight the reactivity of halogenated benzenes and their potential use in synthesizing labeled compounds for imaging and tracing studies.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated benzenes are influenced by the nature and position of the halogen substituents. The presence of bromine and fluorine atoms affects the geometry of the benzene ring and its vibrational modes. The solvent effect on NMR spectral parameters has been observed, indicating that the environment can significantly impact the properties of these molecules. Additionally, thermodynamic properties such as heat capacities, entropies, and enthalpy changes have been calculated, providing further understanding of the stability and reactivity of these compounds.

Scientific Research Applications

Application 1: Preparation of 3′-bromo-2,3,4,5,6-pentaethyl-biphenyl

• Summary of the Application : 1-Bromo-3-iodobenzene is used in the preparation of 3′-bromo-2,3,4,5,6-pentaethyl-biphenyl.
• Methods of Application : This compound is prepared by reacting 1-Bromo-3-iodobenzene with hex-3-yne.
• Results or Outcomes : The reaction results in the formation of 3′-bromo-2,3,4,5,6-pentaethyl-biphenyl.

Application 2: Preparation of Fluorinated Compounds

• Summary of the Application : 1-Bromo-3-iodobenzene is also used to prepare 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene.
• Methods of Application : The specific methods of application or experimental procedures were not provided in the source.
• Results or Outcomes : The reaction results in the formation of fluorinated compounds.

Safety And Hazards

The compound has been classified with the GHS07 pictogram. The hazard statements associated with it are H302, H315, H319, H332, and H335. Precautionary measures include P261, P280, and P305+P351+P338.

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