Production Method 1

147460-41-1

871717-61-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  2 h, rt

Reference

Effect of ligand electronic properties on precatalyst initiation and propagation in Ni-catalyzed cross-coupling polymerizations

Lee, Se Ryeon; et al, Chemical Science, 2012, 3(5), 1562-1566

Production Method 2

348-57-2

871717-61-2

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: 1,4-Dioxane ;  5 min, rt
1.2 6 h, rt
1.3 Reagents: Water ;  rt

Reference

Regioselective SNAr reactions of substituted difluorobenzene derivatives: practical synthesis of fluoroaryl ethers and substituted resorcinols

Ouellet, Stephane G.; et al, Tetrahedron Letters, 2009, 50(27), 3776-3779

1-Bromo-2-ethoxy-4-fluorobenzene Raw materials

• 2-Bromo-5-fluorophenol
• 1-Bromo-2,4-difluorobenzene

1-Bromo-2-ethoxy-4-fluorobenzene Preparation Products

• 1-Bromo-2-ethoxy-4-fluorobenzene (871717-61-2)

• 1. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
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• 4. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 5. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Phenol ethers
• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers

Chemical Profile of 1-Bromo-2-ethoxy-4-fluorobenzene (CAS No. 871717-61-2)

1-Bromo-2-ethoxy-4-fluorobenzene, identified by its CAS number 871717-61-2, is a fluorinated aromatic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound serves as a versatile intermediate in the synthesis of various biologically active molecules, particularly those targeting neurological and cardiovascular diseases. The unique structural features of this molecule, including the presence of both bromine and ethoxy substituents on a fluorobenzene backbone, make it an attractive scaffold for medicinal chemists seeking to develop novel therapeutic agents.

The fluorine atom in 1-bromo-2-ethoxy-4-fluorobenzene plays a crucial role in modulating the pharmacokinetic and pharmacodynamic properties of derived compounds. Fluorine substitution is well-documented to enhance metabolic stability, improve binding affinity to biological targets, and influence drug distribution. Recent studies have highlighted the importance of fluorinated aromatic compounds in the development of next-generation antiviral and anticancer agents, where the electron-withdrawing nature of fluorine contributes to increased potency and selectivity.

In the context of drug discovery, 1-bromo-2-ethoxy-4-fluorobenzene has been utilized as a key building block in the synthesis of small-molecule inhibitors targeting enzyme-catalyzed pathways. For instance, researchers have explored its potential in developing kinase inhibitors, where the bromine substituent facilitates further functionalization via cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings. These transformations allow for the introduction of diverse pharmacophores, enabling fine-tuning of biological activity.

Moreover, the ethoxy group in 1-bromo-2-ethoxy-4-fluorobenzene contributes to the compound's solubility and lipophilicity balance, which are critical factors in drug formulation and delivery. The presence of this moiety can also influence receptor binding interactions, as evidenced by computational studies demonstrating its role in stabilizing protein-ligand complexes. Such insights have guided the design of analogs with improved pharmacological profiles.

Recent advancements in flow chemistry have further expanded the synthetic applications of 1-bromo-2-ethoxy-4-fluorobenzene. Continuous-flow reactors enable efficient preparation of fluorinated intermediates under controlled conditions, reducing reaction times and improving yields. This approach is particularly advantageous for large-scale production, where reproducibility and scalability are paramount. Additionally, green chemistry principles have been integrated into these processes, minimizing waste generation and hazardous solvent use.

The pharmaceutical industry has shown particular interest in derivatives of 1-bromo-2-ethoxy-4-fluorobenzene due to their potential in treating neurological disorders. Preclinical studies have demonstrated that certain analogs exhibit neuroprotective effects by modulating neurotransmitter receptor activity. The fluorine atom's ability to fine-tune electronic properties makes it an ideal candidate for designing molecules that interact selectively with serotonin or dopamine receptors, which are implicated in conditions such as depression and Parkinson's disease.

In agrochemical research, 1-bromo-2-ethoxy-4-fluorobenzene has been employed in the synthesis of novel herbicides and fungicides. The structural motif is found to confer resistance against degradation by environmental factors, ensuring prolonged efficacy in crop protection applications. Researchers have leveraged its reactivity to introduce additional functional groups that enhance bioavailability and target specificity, aligning with global efforts to develop sustainable agricultural solutions.

The chemical properties of 1-bromo-2-ethoxy-4-fluorobenzene also make it a valuable tool for material science applications. Fluorinated aromatic compounds are known for their thermal stability and electronic conductivity, making them suitable for use in organic light-emitting diodes (OLEDs) and liquid crystal displays (LCDs). Ongoing work explores its incorporation into advanced polymers that could revolutionize electronic device manufacturing.

In conclusion, 1-bromo-2-ethoxy-4-fluorobenzene (CAS No. 871717-61-2) represents a multifaceted compound with broad utility across multiple scientific disciplines. Its unique structural features enable diverse synthetic pathways, making it indispensable in pharmaceutical development. As research continues to uncover new applications for fluorinated aromatic compounds, the significance of this intermediate is expected to grow further, driving innovation in medicine and beyond.

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