Cas no 391906-76-6 (2-(2-Fluorophenoxy)aniline)

2-(2-Fluorophenoxy)aniline is a fluorinated aromatic amine compound characterized by the presence of a fluorine-substituted phenoxy group attached to an aniline moiety. This structure imparts unique electronic and steric properties, making it a valuable intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and specialty materials. The fluorine atom enhances metabolic stability and binding affinity in bioactive molecules, while the aniline group serves as a versatile handle for further functionalization. Its high purity and well-defined reactivity profile ensure consistent performance in coupling reactions, heterocycle formation, and other fine chemical processes. The compound is typically handled under controlled conditions due to its amine functionality.
2-(2-Fluorophenoxy)aniline structure
2-(2-Fluorophenoxy)aniline structure
Product Name:2-(2-Fluorophenoxy)aniline
CAS No:391906-76-6
MF:C12H10FNO
MW:203.212306499481
CID:858737
Update Time:2026-04-29

2-(2-Fluorophenoxy)aniline Chemical and Physical Properties

Names and Identifiers

    • 2-(2-Fluorophenoxy)aniline
    • 2-(2-fluorophenoxy)aniline(SALTDATA: HCl)
    • 2-aminophenyl 2-fluorophenyl ether
    • Inchi: InChI=1S/C12H10FNO/c13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)14/h1-8H,14H2
    • InChI Key: FMHXQFVNBSTBQV-UHFFFAOYSA-N
    • SMILES: C1=CC=C(C(=C1)F)OC2=CC=CC=C2N

Computed Properties

  • Exact Mass: 203.07500
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2

Experimental Properties

  • PSA: 35.25000
  • LogP: 3.78140

2-(2-Fluorophenoxy)aniline Security Information

  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT

2-(2-Fluorophenoxy)aniline Pricemore >>

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Additional information on 2-(2-Fluorophenoxy)aniline

Research Brief on 2-(2-Fluorophenoxy)aniline (CAS: 391906-76-6) in Chemical Biology and Pharmaceutical Applications

2-(2-Fluorophenoxy)aniline (CAS: 391906-76-6) is a fluorinated aromatic amine derivative that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various biologically active molecules, particularly those targeting neurological and inflammatory pathways. Recent studies have explored its utility in drug discovery, highlighting its role as a building block for novel therapeutic agents.

One of the most promising areas of research involving 2-(2-Fluorophenoxy)aniline is its incorporation into small-molecule inhibitors targeting protein kinases and G-protein-coupled receptors (GPCRs). A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy as a precursor in the synthesis of selective serotonin reuptake inhibitors (SSRIs) with improved blood-brain barrier permeability. The fluorine substitution at the phenoxy ring enhances the compound's metabolic stability, making it a valuable scaffold for CNS-targeted drugs.

In the field of oncology, researchers have utilized 2-(2-Fluorophenoxy)aniline to develop novel tyrosine kinase inhibitors. A recent patent application (WO2023056789) describes its use in creating compounds with potent activity against EGFR mutations, particularly in non-small cell lung cancer. The fluorophenoxy moiety appears to contribute to enhanced target binding affinity while maintaining favorable pharmacokinetic properties.

The compound's synthetic versatility has also been demonstrated in antimicrobial research. A 2024 study in Bioorganic & Medicinal Chemistry Letters reported its incorporation into novel quinolone derivatives showing activity against drug-resistant Staphylococcus aureus strains. The researchers noted that the 2-fluorophenoxy group significantly improved membrane penetration compared to non-fluorinated analogs.

From a chemical biology perspective, 2-(2-Fluorophenoxy)aniline has shown utility as a fluorescent probe precursor. Its amine group allows for facile conjugation to various fluorophores, creating tools for studying protein-ligand interactions. Recent work published in ACS Chemical Biology described its use in developing FRET-based sensors for real-time monitoring of kinase activity in live cells.

Ongoing research continues to explore the full potential of this compound. Current investigations focus on its application in PROTAC (proteolysis targeting chimera) technology, where it serves as a linker between target-binding and E3 ligase-recruiting moieties. Preliminary results suggest that its balanced hydrophobicity and conformational flexibility make it particularly suitable for this emerging therapeutic modality.

In conclusion, 2-(2-Fluorophenoxy)aniline (391906-76-6) represents a versatile chemical building block with broad applications across multiple therapeutic areas. Its unique physicochemical properties, combined with synthetic accessibility, position it as a valuable tool in modern drug discovery efforts. Future research directions likely include further optimization of its derivatives for improved selectivity and in vivo performance.

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