• 1. An antioxidant self-healing hydrogel for 3D cell cultures?
  Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei Tao J. Mater. Chem. B, 2020,8, 1383-1388
• 2. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 3. Alternative mixtures to R-600a. Theoretical assessment and experimental energy evaluation of binary mixtures in a commercial cooler: Mélanges alternatifs au R-600a. évaluation théorique et évaluation énergétique expérimentale de mélanges binaires dans un refroidisseur commercial.
  DanielCalleja-Anta,DanielSánchez,LauraNebot-Andres,RamónCabello,RodrigoLlopis
• 4. An aptasensor for the detection of ampicillin in milk using a personal glucose meter
  Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381
• 5. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Anisoles

2-Bromo-1,4-difluoro-3-methoxybenzene (CAS No. 1208076-11-2): An Overview and Recent Advances

2-Bromo-1,4-difluoro-3-methoxybenzene (CAS No. 1208076-11-2) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound, characterized by its unique bromine, fluorine, and methoxy functional groups, exhibits a range of chemical properties that make it an attractive candidate for various applications. In this article, we will delve into the chemical structure, synthesis methods, and recent research developments involving 2-Bromo-1,4-difluoro-3-methoxybenzene.

Chemical Structure and Properties

2-Bromo-1,4-difluoro-3-methoxybenzene is a substituted benzene derivative with a bromine atom at the 2-position, two fluorine atoms at the 1 and 4 positions, and a methoxy group at the 3-position. The presence of these functional groups imparts distinct chemical and physical properties to the molecule. The bromine atom provides electrophilic reactivity, making it useful in coupling reactions. The fluorine atoms enhance the molecule's lipophilicity and metabolic stability, which are crucial for drug design. The methoxy group contributes to the molecule's solubility and electronic properties.

The molecular formula of 2-Bromo-1,4-difluoro-3-methoxybenzene is C₈H₅BrF₂O, with a molecular weight of approximately 235.03 g/mol. It is typically a white to off-white solid at room temperature and is soluble in common organic solvents such as dichloromethane, ethyl acetate, and dimethyl sulfoxide (DMSO).

Synthesis Methods

The synthesis of 2-Bromo-1,4-difluoro-3-methoxybenzene can be achieved through various routes, depending on the availability of starting materials and the desired yield and purity. One common method involves the bromination of 1,4-difluoro-3-methoxybenzene using bromine or a brominating agent such as N-bromosuccinimide (NBS). This reaction typically proceeds under mild conditions and can be optimized to achieve high yields.

An alternative approach involves the selective fluorination of 2-bromo-3-methoxybenzene using a fluorinating agent such as Selectfluor or diethylaminosulfur trifluoride (DAST). This method allows for precise control over the placement of fluorine atoms on the benzene ring.

Applications in Medicinal Chemistry

2-Bromo-1,4-difluoro-3-methoxybenzene has found applications in medicinal chemistry due to its unique combination of functional groups. One notable area of research involves its use as an intermediate in the synthesis of potential therapeutic agents. For example, recent studies have explored its role in the development of novel antiviral compounds targeting viral proteases.

A study published in the Journal of Medicinal Chemistry reported the synthesis of a series of derivatives based on 2-Bromo-1,4-difluoro-3-methoxybenzene, which exhibited potent antiviral activity against influenza A virus. The researchers found that the presence of the bromine and fluorine atoms significantly enhanced the inhibitory activity of these compounds against viral proteases.

In another study, researchers investigated the use of 2-Bromo-1,4-difluoro-3-methoxybenzene-based compounds as potential anticancer agents. The results showed that these derivatives displayed selective cytotoxicity against various cancer cell lines while showing minimal toxicity to normal cells. The enhanced lipophilicity and metabolic stability conferred by the fluorine atoms were identified as key factors contributing to their biological activity.

Molecular Modeling and Computational Studies

Molecular modeling and computational studies have played a crucial role in understanding the structure-property relationships of 2-Bromo-1,4-difluoro-3-methoxybenzene. These studies provide valuable insights into the electronic structure and reactivity patterns of the molecule, which can guide synthetic efforts and drug design.

A recent computational study using density functional theory (DFT) revealed that the electronic properties of 2-Bromo-1,4-difluoro-3-methoxybenzene, particularly its frontier molecular orbitals (HOMO and LUMO), are significantly influenced by the presence of bromine and fluorine atoms. The results indicated that these functional groups enhance the molecule's electrophilic reactivity and improve its binding affinity to biological targets.

FUTURE DIRECTIONS AND CONCLUSIONS

The ongoing research on 2-Bromo-1,4-difluoro-3-methoxybenzene highlights its potential as a valuable building block in medicinal chemistry and materials science. Future studies are likely to focus on optimizing its synthesis methods to improve yield and purity while exploring new applications in drug discovery and materials development.

In conclusion, 2-Bromo-1,4-difluoro-3-methoxybenzene (CAS No. 1208076-11-2) is a promising compound with a unique combination of functional groups that offer diverse chemical properties. Its applications in medicinal chemistry are particularly noteworthy, with recent studies demonstrating its potential as an intermediate in the synthesis of antiviral and anticancer agents. As research continues to advance, this compound is poised to play an increasingly important role in various scientific fields.

• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)