1-Bromo-2,4,5-trifluoro-3-methoxybenzene
[CAS# 13332-24-6]

Identification

• Classification: Organic raw materials >> Organic fluorine compound
• Name: 1-Bromo-2,4,5-trifluoro-3-methoxybenzene
• Molecular Formula: C₇H₄BrF₃O
• Molecular Weight: 241.01
• CAS Registry Number: 13332-24-6
• SMILES: COC1=C(C(=CC(=C1F)Br)F)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Discovery and Applications

1-Bromo-2,4,5-trifluoro-3-methoxybenzene is an aromatic halogenated compound, which consists of a benzene ring substituted with a bromine atom at the 1-position, three fluorine atoms at the 2, 4, and 5-positions, and a methoxy group (-OCH₃) at the 3-position. This structure is a member of the halogenated and fluorinated aromatic compounds, which are of interest in various chemical, pharmaceutical, and materials science applications due to their unique properties imparted by the combination of electronegative substituents.

The compound is primarily used in synthetic chemistry as an intermediate in the preparation of more complex molecules. The trifluoromethyl group (-CF₃) and the methoxy group (-OCH₃) are both electron-donating groups, which can influence the reactivity and solubility of the molecule. The fluorine atoms contribute to the compound's stability, as the C-F bond is highly polar and strong. These substituents can also modify the molecule's electronic characteristics, making it useful in applications where electronic effects play a critical role.

The bromine atom, being a halogen, makes the molecule reactive and useful in nucleophilic substitution reactions. The position of the bromine on the benzene ring (at the 1-position) allows for specific types of reactions, such as cross-coupling reactions or halogen exchange reactions, which are frequently used in the synthesis of complex organic compounds.

The methoxy group (-OCH₃) is an electron-donating group via resonance, which can further influence the reactivity of the molecule, typically making it more reactive toward electrophilic substitution reactions. The presence of both electronegative (fluorine) and electron-donating (methoxy) groups in the same molecule creates interesting opportunities for tuning the reactivity and selectivity of chemical reactions.

This compound has found use in the development of materials and pharmaceuticals, where its halogenated and methoxy-substituted structure can modulate the properties of polymers, agrochemicals, or drug-like molecules. The trifluoromethyl and methoxy groups are often incorporated in the synthesis of bioactive compounds to improve pharmacokinetic properties such as solubility, stability, and bioavailability. Additionally, halogenated aromatic compounds like 1-bromo-2,4,5-trifluoro-3-methoxybenzene are commonly studied for their role in modifying the properties of small molecules and for their potential applications in organic electronics, such as OLEDs (organic light-emitting diodes) and organic semiconductors.

In conclusion, 1-bromo-2,4,5-trifluoro-3-methoxybenzene is a versatile intermediate in organic synthesis, useful in the preparation of more complex fluorinated and halogenated compounds, as well as in the development of pharmaceutical and material science applications. The combination of bromine, fluorine, and methoxy groups provides a unique set of reactivity and electronic properties that enable the compound to serve as a building block in various chemical processes.

References

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