261951-96-6 | 2-Bromo-5-(trifluoromethoxy)toluene

CAS:261951-96-6 | 2-Bromo-5-(trifluoromethoxy)toluene,Description

Synthesis Analysis

The synthesis of derivatives similar to 1-Bromo-2-methyl-4-(trifluoromethoxy)benzene involves multiple steps including bromination, nucleophilic substitution, and the use of lithium diisopropylamide (LDA) as a base to generate intermediates which can undergo further chemical transformations. The generation of arynes from brominated precursors and their subsequent reactions to form more complex structures is a notable pathway (Schlosser & Castagnetti, 2001).

Molecular Structure Analysis

The molecular structure of bromo- and bromomethyl-substituted benzenes has been studied through X-ray crystallography, revealing interactions such as C–H···Br, C–Br···Br, and C–Br···π. These interactions contribute to the understanding of the packing motifs in the solid state and have implications for the reactivity and stability of these compounds (Jones, Kuś, & Dix, 2012).

Chemical Reactions and Properties

1-Bromo-2-methyl-4-(trifluoromethoxy)benzene participates in various chemical reactions, including those leading to the formation of organometallic intermediates and those involving radical additions in aqueous media. Such reactions highlight the compound's versatility as a precursor for further chemical synthesis, with its reactivity influenced by the presence of bromo- and trifluoromethoxy groups (Porwisiak & Schlosser, 1996).

Physical Properties Analysis

The physical properties of bromo-substituted benzenes, including those related to 1-Bromo-2-methyl-4-(trifluoromethoxy)benzene, are determined by their molecular structure. Properties such as melting points, boiling points, and solubility are influenced by the specific substituents present on the benzene ring. These properties are essential for determining the conditions under which these compounds can be handled and used in laboratory or industrial settings.

Chemical Properties Analysis

The chemical properties of 1-Bromo-2-methyl-4-(trifluoromethoxy)benzene are characterized by its reactivity towards nucleophiles, electrophiles, and radicals. Its ability to undergo substitution reactions, participate in organometallic synthesis, and act as a precursor for the synthesis of complex molecules underscores its importance in organic chemistry. The presence of the trifluoromethoxy group also imparts unique electronic effects that influence its reactivity and stability (Reus et al., 2012).

Scientific Research Applications

Synthesis and Intermediates

1-Bromo-2-methyl-4-(trifluoromethoxy)benzene is utilized in the synthesis of complex organic compounds, demonstrating its versatility as an intermediate. For example, it is involved in the generation of 1,2-dehydro-4-(trifluoromethoxy)benzene through treatment with lithium diisopropylamide, leading to various naphthalenes and naphthols upon further reactions. This pathway highlights its role in constructing intricate molecular structures, showcasing its importance in synthetic organic chemistry (Schlosser & Castagnetti, 2001).

Fluorine Chemistry and Organometallic Synthesis

The compound is also significant in the field of fluorine chemistry and organometallic synthesis. The ability to generate trifluoromethoxide anions for SN2 reactions and form trifluoromethyl ethers underscores its utility in introducing fluorine-containing groups into molecules. This is particularly relevant for the development of materials with unique properties, such as increased stability or novel reactivity patterns (Duran-Camacho et al., 2021).

Nucleophilic Displacement and Functional Group Transformation

The capacity for nucleophilic displacement by the trifluoromethoxide anion from activated aromatic rings to form aliphatic trifluoromethyl ethers is another key application. This exemplifies its role in functional group transformations, providing a pathway to alter molecular structures for various research and development purposes (Marrec et al., 2010).

Structural Studies and Crystallography

In addition to synthetic applications, 1-Bromo-2-methyl-4-(trifluoromethoxy)benzene and related compounds are subjects of structural studies to understand molecular interactions, such as C–H···Br, C–Br···Br, and C–Br···π interactions. These studies provide insights into the molecular packing, intermolecular forces, and the influence of substituents on crystal structures, contributing to the fundamental knowledge in crystallography and materials science (Jones et al., 2012).

Safety And Hazards

Exposure to 1-Bromo-2-methyl-4-(trifluoromethoxy)benzene should be avoided as it can cause respiratory tract irritation and may lead to pulmonary edema . It is recommended to avoid breathing its mist, gas, or vapors, and to avoid contact with skin and eyes . Use of personal protective equipment and chemical impermeable gloves is advised .

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