4-(4-Nitrophenyl)morpholine
[CAS# 10389-51-2]

Identification

• Name: 4-(4-Nitrophenyl)morpholine
• Synonyms: p-Morpholinonitrobenzene
• Molecular Formula: C₁₀H₁₂N₂O₃
• Molecular Weight: 208.21
• CAS Registry Number: 10389-51-2
• EC Number: 233-851-3
• SMILES: C1COCCN1C2=CC=C(C=C2)[N+](=O)[O-]

Properties

• Melting point: 148-152 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

4-(4-Nitrophenyl)morpholine is an organic compound that has garnered attention due to its unique structure and versatile applications in various fields of chemistry. The compound consists of a morpholine ring substituted with a 4-nitrophenyl group, which imparts distinct chemical properties. The discovery of 4-(4-nitrophenyl)morpholine can be linked to the broader exploration of morpholine derivatives in the mid-20th century when researchers were particularly interested in understanding the reactivity and potential applications of nitrogen-containing heterocycles.

The synthesis of 4-(4-nitrophenyl)morpholine typically involves the reaction of morpholine with 4-nitrochlorobenzene in the presence of a base, such as potassium carbonate. This nucleophilic aromatic substitution reaction allows the nitrogen atom in morpholine to replace the chlorine atom in 4-nitrochlorobenzene, resulting in the formation of 4-(4-nitrophenyl)morpholine. The nitro group on the benzene ring significantly influences the electronic properties of the compound, making it an interesting subject for further study.

One of the primary applications of 4-(4-nitrophenyl)morpholine is in the development of pharmaceuticals and agrochemicals. The compound's structural framework serves as a building block in the synthesis of various biologically active molecules. For instance, derivatives of 4-(4-nitrophenyl)morpholine have been explored for their potential as anti-inflammatory, antimicrobial, and anticancer agents. The presence of both the morpholine ring and the nitro group provides a platform for further functionalization, enabling the design of compounds with specific biological activities.

In the field of materials science, 4-(4-nitrophenyl)morpholine has been studied for its potential use in the development of novel polymers and dyes. The nitro group on the benzene ring can undergo reduction to form an amino group, which can then participate in various polymerization reactions. This allows for the incorporation of 4-(4-nitrophenyl)morpholine into polymeric materials, potentially imparting unique mechanical, thermal, or optical properties. Additionally, the compound has been used as an intermediate in the synthesis of azo dyes, which are important in textile and printing industries due to their vibrant colors and stability.

Another notable application of 4-(4-nitrophenyl)morpholine is in organic synthesis as a reagent or catalyst. The compound's ability to participate in nucleophilic substitution reactions makes it a valuable tool for introducing the 4-nitrophenyl group into other organic molecules. This functional group can then be further modified, making 4-(4-nitrophenyl)morpholine a versatile intermediate in the synthesis of more complex organic compounds.

Moreover, 4-(4-nitrophenyl)morpholine has been investigated for its potential environmental applications. Due to its nitro functionality, the compound can be used in the study of environmental pollutants, particularly in understanding the behavior and degradation of nitroaromatic compounds in the environment. Research in this area aims to develop methods for the detection and remediation of such pollutants, with 4-(4-nitrophenyl)morpholine serving as a model compound in these studies.

In summary, 4-(4-nitrophenyl)morpholine is a compound with diverse applications in pharmaceuticals, materials science, organic synthesis, and environmental chemistry. Its discovery has paved the way for the development of a wide range of compounds and materials, demonstrating the importance of morpholine derivatives in modern chemical research.

References

2012. 4-(4-Nitro-phen-yl)morpholine. Acta Crystallographica Section E, Structure Reports Online, 68(4), o1217.
DOI: 10.1107/s1600536812012172

2022. Gold nanoparticle-decorated earth-abundant clay nanotubes as catalyst for the degradation of phenothiazine dyes and reduction of 4-(4-nitrophenyl)morpholine. Environmental Science and Pollution Research International, 29(30), 45454-46466.
DOI: 10.1007/s11356-022-19523-1

2005. Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents. European Journal of Medicinal Chemistry, 40(2), 155-159.
DOI: 10.1016/j.ejmech.2004.09.003