452-74-4 | 4-Bromo-3-fluorotoluene

CAS:452-74-4 | 4-Bromo-3-fluorotoluene,Description

Synthesis Analysis

The synthesis of derivatives similar to 4-Bromo-3-fluorotoluene, such as 4-Fluoro-3-phenoxytoluene, involves Ullmann coupling reactions, indicating a general approach that could be adapted for 4-Bromo-3-fluorotoluene synthesis (Zhao Wenxian, Wang De-kun, & Z. Yanli, 2004). Such methods typically involve the reaction of halogenated toluenes with phenols or other nucleophiles in the presence of copper catalysts.

Molecular Structure Analysis

The molecular structure of 4-Bromo-3-fluorotoluene is characterized by the presence of bromo and fluoro substituents on the phenyl ring of toluene. These substituents influence the electronic properties of the molecule, as seen in compounds with similar structures. For example, the structural properties and quantum chemical analysis on a chalcone derivative show the impact of halogen substituents on the molecule's electronic properties, suggesting similar effects in 4-Bromo-3-fluorotoluene (M. F. Zaini, S. Arshad, A. R. Ibrahim, N. Che Khalib, & D. A. Zainuri, 2018).

Scientific Research Applications

• Radioiodinated Precursors : A study demonstrated that no-carrier-added (4-fluoro-3-[131I]iodobenzyl)guanidine can be prepared using radioiodination to produce stable silicon precursors with high radiochemical yields and minimal byproduct formation, indicating potential use in medical imaging and diagnostics (Vaidyanathan, Affleck, & Zalutsky, 1996).
• Synthesis of Organic Compounds : The synthesis of Methyl 4-bromo-2-methoxybenzoate from 4-bromo-2-fluorotoluene has been achieved with a yield of 47% and a purity of 99.8%, demonstrating its utility in organic synthesis (Chen, 2008).
• Electrochemical Bromination : Research on electrochemical bromination of 4-methoxy toluene has yielded 3-bromo 4-methoxy benzyl bromide in 86% yield, providing insights into the orientation of bromine atoms in alkyl aromatic compounds (Kulangiappar, Anbukulandainathan, & Raju, 2014).
• Electronic Absorption Spectra : The electronic absorption spectra of various fluorotoluene derivatives have been studied to reveal transitions and ground state fundamentals, contributing to our understanding of their electronic properties (Dwivedi & Sharma, 1974).
• Fluorescence Imaging : 4-Bromo-1,8-naphthalimide derivatives are useful for fluorescence imaging and intracellular detection of GSTP1 activity in living cells, enabling the distinction between cancer cells and normal cells (Fujikawa et al., 2019).
• Thermodynamic Properties : A study on 4-fluorotoluene explored its chemical thermodynamic properties in the ideal-gas state, with vibrational assignment consistent with calorimetric data (Scott et al., 1962) .
• High-Pressure Crystallization : Research on high-pressure crystallization of fluorotoluene isomers revealed different polymorphic forms compared to low-temperature crystallization, highlighting the effects of temperature and pressure on crystallization in weak hydrogen bonds (Ridout & Probert, 2013) .
• Catalysis in Organic Reactions : Supported Pd nanoparticles on COOH-modified graphene have been used to catalyze Suzuki-Miyaura C-C coupling reactions for the preparation of fluorinated biphenyl derivatives, demonstrating the compound's role in facilitating chemical reactions (Sadeghi Erami et al., 2017).
• Solid Acid Catalysts in Nitration : Solid acid catalysts have been found effective in the regioselective nitration of fluorotoluenes, providing a cleaner and environmentally friendlier process (Maurya et al., 2003).
• Fungal Metabolism of Toluene : Studies on fungal metabolism of toluene, using fluorinated analogs, have shown that fungi growing on toluene as their sole carbon and energy source assimilate it by initially oxidizing the methyl group (Prenafeta-Boldú et al., 2001) .

Safety And Hazards

4-Bromo-3-fluorotoluene is considered hazardous. It is classified as a flammable liquid, skin irritant, serious eye irritant, and may cause respiratory irritation. Safety measures include avoiding dust formation, avoiding breathing mist, gas or vapors, avoiding contact with skin and eyes, and using personal protective equipment.

Relevant Papers A patent titled “Preparation of 3-bromo-4-fluorotoluene” describes the preparation of 3-bromo-4-fluorotoluene by reacting 4-fluorotoluene with bromine. The bromination is carried out in glacial acetic acid in the presence of iodine and iron or an iron salt. This process results in a significantly higher yield of 3-bromo-4-fluorotoluene compared to prior art processes.

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