2-((4-(2-Fluorophenoxy)phenyl)amino)acetonitrile
[CAS# 1415932-47-6]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 2-((4-(2-Fluorophenoxy)phenyl)amino)acetonitrile
• Synonyms: benzyl 4-nitrophenyl sulfide
• Molecular Formula: C₁₃H₁₁NO₂S
• Molecular Weight: 245.30
• CAS Registry Number: 1415932-47-6
• SMILES: O=[N+]([O-])c1ccc(SCc2ccccc2)cc1

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 399.8±35.0 °C 760 mmHg (Calc.)^*
• Flash point: 195.6±25.9 °C (Calc.)^*
• Index of refraction: 1.648 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

2-((4-(2-Fluorophenoxy)phenyl)amino)acetonitrile is an aromatic nitrile featuring a secondary aniline core substituted by a 2‑fluorophenoxy group and bearing a –CH₂–CN side chain on the aniline nitrogen. The combination of an electron‑withdrawing nitrile group and an electron‑modulating fluorophenoxy unit results in a scaffold with distinct electronic asymmetry across the molecule. This arrangement supports diverse reactivity at both the aromatic system and the benzylic nitrile moiety.

Structurally, the molecule integrates three key components. The aniline substructure provides a hydrogen‑bond donor and contributes to aromatic conjugation. The aryl–O–aryl linkage introduces conformational flexibility and can influence lipophilicity. The terminal nitrile offers a linear polar functionality capable of engaging in further chemical elaboration.

In organic synthesis, this compound is valued as an intermediate for preparing more elaborated aryl ether–aniline frameworks. The nitrile group can be transformed into numerous functional motifs, and the fluorophenoxy substitution enables exploration of structure–property relationships within substituted biphenyl ether series.

In medicinal chemistry, analogous aryl ether–aniline nitriles are studied for their potential to form interactions with biological macromolecules via aromatic stacking, hydrogen bonding, and dipolar contacts associated with the nitrile. The modular architecture permits adjustment of physicochemical properties such as lipophilicity, polarity, and conformational behavior through selective modification of either aromatic ring or the nitrile-bearing side chain.

From a physical standpoint, the compound is typically obtained as a solid or viscous oil, with solubility in common organic media such as chlorinated solvents and polar aprotic solvents. The aryl ether linkage and nitrile functionality contribute to overall stability under standard laboratory storage conditions when kept sealed and protected from prolonged light exposure.

Overall, 2-((4-(2-fluorophenoxy)phenyl)amino)acetonitrile is a functionalized aromatic nitrile whose combination of anilide, aryl‑ether, and nitrile features makes it a useful intermediate and modular building block in exploratory synthesis and structure–activity investigations.

References

none