4-(2-Fluoro-4-nitrophenyl)morpholine
[CAS# 2689-39-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 4-(2-Fluoro-4-nitrophenyl)morpholine
• Synonyms: N-(2-Fluoro-4-nitrophenyl)morpholine
• Molecular Formula: C₁₀H₁₁FN₂O₃
• Molecular Weight: 226.20
• CAS Registry Number: 2689-39-6
• SMILES: C1COCCN1C2=C(C=C(C=C2)[N+](=O)[O-])F

Properties

• Solubility: Slightly soluble (1.3 g/L) (25 °C), Calc.^*
• Density: 1.340±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 121-126 °C^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Reddy, Ganta Madhusudhan

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

4-(2-Fluoro-4-nitrophenyl)morpholine is a chemical compound that has garnered attention in the fields of medicinal chemistry and chemical synthesis due to its unique structure and versatile applications. This compound features a morpholine ring—an organic heterocyclic compound containing both nitrogen and oxygen—substituted with a 2-fluoro-4-nitrophenyl group.

The discovery of 4-(2-fluoro-4-nitrophenyl)morpholine can be traced back to studies on morpholine derivatives, which have been explored for their potential biological and chemical properties. The introduction of the fluoro and nitro groups into the phenyl ring adds distinctive electronic and steric effects, making this compound of particular interest for various applications.

One of the primary applications of 4-(2-fluoro-4-nitrophenyl)morpholine is in medicinal chemistry, where it serves as an important intermediate in the synthesis of pharmaceutical agents. The compound’s ability to act as a key building block allows for the development of novel drugs with enhanced biological activity. For instance, its structure can be leveraged to design inhibitors for various biological targets, including enzymes and receptors. The presence of the fluoro and nitro substituents can influence the electronic properties of the compound, potentially leading to improved potency and selectivity in drug candidates.

In addition to its role in drug development, 4-(2-fluoro-4-nitrophenyl)morpholine is used in the synthesis of complex organic molecules. The compound's morpholine ring offers a versatile platform for further chemical modifications, while the 2-fluoro-4-nitrophenyl group introduces functional diversity. These properties are useful in the creation of complex molecular structures that can be applied in various research and industrial settings.

The synthesis of 4-(2-fluoro-4-nitrophenyl)morpholine typically involves the reaction of a morpholine derivative with 2-fluoro-4-nitrobenzaldehyde or similar reagents. This process requires precise control of reaction conditions to ensure high yields and purity of the product. The resulting compound can then be used as a precursor for further chemical transformations.

In summary, 4-(2-fluoro-4-nitrophenyl)morpholine is a valuable compound in both medicinal chemistry and chemical synthesis. Its unique structure, characterized by the morpholine ring and the fluoro-nitro substituted phenyl group, provides a versatile platform for the development of new drugs and complex organic molecules. The continued exploration of its applications and derivatives holds promise for advancing both pharmaceutical research and chemical synthesis.

References

2022. Synthesis, Docking and Antibacterial Evaluation of N-(1-(3-Fluoro-4-morpholinophenyl)-1H-tetrazol-5-yl) Amides. Chemistry Africa, 5(3).
DOI: 10.1007/s42250-022-00347-y

2017. Sulfonamides and carbamates of 3-fluoro-4-morpholinoaniline (linezolid intermediate): synthesis, antimicrobial activity and molecular docking study. Research on Chemical Intermediates, 43(12).
DOI: 10.1007/s11164-017-3114-1

2019. Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates. Synthesis, 51(10).
DOI: 10.1055/s-0037-1610714