450412-29-0 | 2-IODO-3-BROMOFLUOROBENZENE

CAS:450412-29-0 | 2-IODO-3-BROMOFLUOROBENZENE,Description

1-Bromo-3-fluoro-2-iodobenzene is a halogenated aromatic compound that has been the subject of various studies due to its potential as a precursor in organic synthesis. The presence of bromine, fluorine, and iodine on the benzene ring makes it a versatile intermediate for constructing more complex molecules through various chemical reactions.

Synthesis Analysis

The synthesis of halogenated benzene derivatives, including 1-bromo-3-fluoro-2-iodobenzene, often involves regioselective halogenation and halogen/metal permutations. For instance, 1,2-dibromobenzenes, which are closely related to the target compound, can be synthesized through sequences that include regioselective bromination and subsequent transformations. Additionally, the preparation of similar compounds like 1-bromo-4-[18F]fluorobenzene has been achieved through nucleophilic aromatic substitution reactions, indicating possible synthetic routes for the target compound.

Molecular Structure Analysis

The molecular structure and vibrational frequencies of 1-bromo-3-fluorobenzene, a compound similar to 1-bromo-3-fluoro-2-iodobenzene, have been studied using Fourier-transform infrared spectroscopy (FT-IR) and Raman spectroscopy, along with density functional theory (DFT) calculations. These studies provide insights into the influence of halogen atoms on the geometry and vibrational modes of the benzene ring, which are relevant for understanding the properties of 1-bromo-3-fluoro-2-iodobenzene.

Chemical Reactions Analysis

1-Bromo-3-fluoro-2-iodobenzene can participate in various chemical reactions due to its reactive halogen substituents. For example, CuI-catalyzed coupling reactions involving 1-bromo-2-iodobenzenes have been shown to produce 2,3-disubstituted benzofurans, demonstrating the potential for intramolecular cyclization reactions. Palladium-catalyzed carbonylative reactions of similar compounds with different nucleophiles have also been reported, leading to the formation of six-membered heterocycles. These studies suggest that 1-bromo-3-fluoro-2-iodobenzene could undergo similar transformations, expanding its utility in organic synthesis.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated benzenes are significantly influenced by their substituents. The electronic properties, such as absorption wavelengths, excitation energy, dipole moment, and frontier molecular orbital energies, have been investigated for related compounds, providing a basis for understanding the reactivity and stability of 1-bromo-3-fluoro-2-iodobenzene. Additionally, the thermodynamic properties, including heat capacities, entropies, and enthalpy changes, have been calculated, which are essential for predicting the behavior of the compound under different conditions.

Scientific Research Applications

• Organic Synthesis Building Block : This compound is primarily used as a building block in organic synthesis. It is used in the preparation of various other compounds.
• Preparation of Specific Compounds : 3-Fluoroiodobenzene, which can be derived from 1-Bromo-3-fluoro-2-iodobenzene, participates in palladium-catalyzed hydroarylation of arylpropiolamides. This process is used to prepare methyl 4-iodobenzo[b]thiophene-2-carboxylate, a key intermediate for the synthesis of 4-substituted benzo[b]thiophene-2-carboxamidines.
• LCD Medium : 1-Bromo-3-Fluoro-4-Iodobenzene can be used for the preparation of 2-(4-[4-(3,5-difluoro-4-(3-methyl)phenyl]-3-fluorophenyl)cyclohex-3-ene-1-yl]-5-propyl-1,3-dioxane, a compound suitable for use in liquid crystal displays (LCDs), especially for TN, STN, IPS, FFS, and TN-TFT displays.
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• Material Science : 1-Bromo-

Safety And Hazards

1-Bromo-3-fluoro-2-iodobenzene is considered hazardous. It has been assigned the GHS07 pictogram. The hazard statements associated with this compound are H302, H315, H319, H335, which indicate that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation.

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Physical Form