Cas no 176175-97-6 (1-(Benzyloxy)-3,5-difluorobenzene)

1-(Benzyloxy)-3,5-difluorobenzene is a fluorinated aromatic ether compound characterized by its benzyloxy and difluoro substituents on the benzene ring. This structure imparts unique electronic and steric properties, making it valuable as an intermediate in organic synthesis, particularly in pharmaceuticals and agrochemicals. The presence of fluorine atoms enhances metabolic stability and lipophilicity, which can be advantageous in drug design. The benzyloxy group offers reactivity for further functionalization, such as deprotection or coupling reactions. Its well-defined molecular architecture ensures consistency in synthetic applications, while its stability under standard conditions facilitates handling and storage. This compound is typically utilized in research and industrial settings for precision chemical transformations.
1-(Benzyloxy)-3,5-difluorobenzene structure
176175-97-6 structure
Product Name:1-(Benzyloxy)-3,5-difluorobenzene
CAS No:176175-97-6
MF:C13H10F2O
MW:220.214710712433
MDL:MFCD18072457
CID:829960
PubChem ID:11736137
Update Time:2025-06-11

1-(Benzyloxy)-3,5-difluorobenzene Chemical and Physical Properties

Names and Identifiers

    • 1-(Benzyloxy)-3,5-difluorobenzene
    • 1,3-difluoro-5-(phenylmethoxy)Benzene
    • 1-Benzyloxy-3,5-difluorobenzene
    • 176175-97-6
    • BHA17597
    • DTXSID70471364
    • Benzene, 1,3-difluoro-5-(phenylmethoxy)-
    • SCHEMBL5042093
    • AS-41288
    • DB-065141
    • 1,3-difluoro-5-phenylmethoxybenzene
    • AKOS016008178
    • MFCD18072457
    • MDL: MFCD18072457
    • Inchi: 1S/C13H10F2O/c14-11-6-12(15)8-13(7-11)16-9-10-4-2-1-3-5-10/h1-8H,9H2
    • InChI Key: PEDMGHKJUCZTHB-UHFFFAOYSA-N
    • SMILES: FC1C=C(C=C(C=1)OCC1C=CC=CC=1)F

Computed Properties

  • Exact Mass: 220.06997126g/mol
  • Monoisotopic Mass: 220.06997126g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 194
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4
  • Topological Polar Surface Area: 9.2?2

Experimental Properties

  • Density: 1.206
  • Boiling Point: 266.001 °C at 760 mmHg
  • Flash Point: 121.942 °C

1-(Benzyloxy)-3,5-difluorobenzene Security Information

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Additional information on 1-(Benzyloxy)-3,5-difluorobenzene

Introduction to 1-(Benzyloxy)-3,5-difluorobenzene (CAS No. 176175-97-6) and Its Emerging Applications in Chemical Biology

1-(Benzyloxy)-3,5-difluorobenzene, identified by the Chemical Abstracts Service number 176175-97-6, is a fluorinated aromatic compound that has garnered significant attention in the field of chemical biology due to its unique structural and electronic properties. The presence of both benzyloxy and fluorine substituents imparts distinct reactivity and binding capabilities, making this molecule a valuable scaffold for the development of novel pharmaceuticals and agrochemicals. This introduction explores the compound's chemical characteristics, synthetic pathways, and its potential applications, particularly in drug discovery and material science, highlighting recent advancements in its utilization.

The molecular structure of 1-(Benzyloxy)-3,5-difluorobenzene consists of a benzene ring substituted with two fluorine atoms at the 3rd and 5th positions, further modified with a benzyloxy group at the 1st position. The fluorine atoms introduce electron-withdrawing effects, which can modulate the reactivity of the aromatic ring, while the benzyloxy group provides a polar moiety that enhances solubility and binding affinity. This combination of functional groups makes the compound highly versatile for medicinal chemistry applications.

From a synthetic perspective, 1-(Benzyloxy)-3,5-difluorobenzene can be prepared through multiple routes, including nucleophilic aromatic substitution (SNAr) on appropriately substituted difluorobenzene precursors or through cross-coupling reactions involving fluorinated aryl halides. Recent studies have demonstrated efficient synthesis methods using palladium-catalyzed coupling reactions, which offer high selectivity and yield under mild conditions. These advancements in synthetic methodology have facilitated access to this compound for further functionalization and derivatization.

In the realm of drug discovery, 1-(Benzyloxy)-3,5-difluorobenzene has been explored as a key intermediate in the synthesis of bioactive molecules. Its structural features make it an ideal candidate for designing ligands that interact with biological targets such as enzymes and receptors. For instance, derivatives of this compound have shown promise in inhibiting certain kinases by mimicking natural substrates or by occupying allosteric sites. The fluorine atoms enhance binding affinity through hydrophobic interactions and π-stacking effects, while the benzyloxy group contributes to hydrogen bonding capabilities.

Recent research has highlighted the utility of 1-(Benzyloxy)-3,5-difluorobenzene in developing small-molecule probes for imaging and diagnostics. The compound's ability to undergo fluorescence quenching or enhancement upon binding to specific biomolecules has been leveraged in F?rster Resonance Energy Transfer (FRET) assays and other high-throughput screening techniques. These applications are particularly relevant in oncology research, where fluorescent probes are used to track tumor progression and identify potential therapeutic targets.

Moreover, the electronic properties of 1-(Benzyloxy)-3,5-difluorobenzene have attracted interest in materials science. Fluorinated aromatic compounds are known for their stability and tunable electronic characteristics, making them suitable for organic semiconductors and light-emitting diodes (OLEDs). Researchers have investigated this compound as a building block for designing novel materials with enhanced charge transport properties. The benzyloxy group also contributes to thermal stability, which is crucial for industrial applications.

The pharmacological potential of 1-(Benzyloxy)-3,5-difluorobenzene has been further explored through computational modeling and experimental validation. Molecular docking studies have revealed its binding interactions with various protein targets, including those involved in metabolic pathways and inflammatory responses. These studies have guided the design of more potent derivatives with improved pharmacokinetic profiles. Additionally, preclinical trials have begun to assess the safety and efficacy of compounds derived from this scaffold in animal models.

The versatility of 1-(Benzyloxy)-3,5-difluorobenzene extends to its role as a catalyst or co-catalyst in organic transformations. Its ability to stabilize reactive intermediates has been exploited in asymmetric synthesis, where chiral auxiliaries or catalysts are employed to achieve enantioselective outcomes. This application is particularly valuable in producing enantiomerically pure drugs that exhibit superior therapeutic effects with fewer side effects.

In conclusion,1-(Benzyloxy)-3,5-difluorobenzene (CAS No. 176175-97-6) represents a promising compound with diverse applications across chemical biology and materials science. Its unique structural features enable its use as an intermediate in drug development, a probe for diagnostic purposes, and a component in advanced materials. Ongoing research continues to uncover new possibilities for this molecule, underscoring its importance as a tool for innovation in both academic and industrial settings.

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