1-(3-Nitrophenyl)pyrrolidine
[CAS# 132993-20-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Pyrroles
• Name: 1-(3-Nitrophenyl)pyrrolidine
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• CAS Registry Number: 132993-20-5
• SMILES: C1CCN(C1)C2=CC(=CC=C2)[N+](=O)[O-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305-P351-P338

Discovory and Applicatios

1-(3-Nitrophenyl)pyrrolidine is a chemical compound that combines a pyrrolidine ring with a 3-nitrophenyl group. The molecular formula for this compound is C11H12N2O2, and its structure features a pyrrolidine ring—a five-membered nitrogen-containing heterocycle—substituted with a nitrophenyl group.

The discovery of 1-(3-Nitrophenyl)pyrrolidine is rooted in the exploration of pyrrolidine derivatives, which are known for their versatility in organic synthesis and medicinal chemistry. Pyrrolidine itself is a common structural motif in many natural and synthetic compounds, contributing to its broad application in various chemical and pharmaceutical contexts. The addition of the nitrophenyl group enhances the compound's utility by introducing electron-withdrawing properties that modify the electronic characteristics of the pyrrolidine ring.

In terms of applications, 1-(3-Nitrophenyl)pyrrolidine is significant for its role in the synthesis of various bioactive molecules. The nitrophenyl group serves as a useful functional handle for further chemical modifications, making this compound a valuable intermediate in the development of pharmaceuticals and agrochemicals. Its reactivity and ability to form new bonds are leveraged in the creation of complex organic molecules.

One of the key applications of 1-(3-Nitrophenyl)pyrrolidine is in the field of medicinal chemistry. The compound is used as a precursor in the synthesis of pharmaceuticals where the pyrrolidine ring is critical for biological activity. For instance, derivatives of pyrrolidine are often found in drugs with therapeutic effects, such as analgesics, antiepileptics, and antihypertensives. The nitro group can be further transformed to introduce additional functional groups that enhance the biological activity or improve the pharmacokinetic properties of the final drug molecules.

In organic synthesis, 1-(3-Nitrophenyl)pyrrolidine is employed in various reaction schemes due to its functional groups. It can participate in nucleophilic substitution reactions, reduction processes, and coupling reactions. The nitro group, being an electron-withdrawing substituent, often makes the pyrrolidine ring more reactive towards nucleophiles, thereby facilitating the formation of complex molecules.

Additionally, this compound can be used as a building block in the synthesis of materials for advanced applications. The electronic properties of the nitrophenyl group and the structural features of the pyrrolidine ring are useful in designing new materials with specific electronic or optical properties. Such materials have potential applications in sensors, electronic devices, and other high-tech fields.

In summary, 1-(3-Nitrophenyl)pyrrolidine is a valuable compound in organic chemistry and medicinal research. Its role as an intermediate in the synthesis of complex molecules and its utility in developing pharmaceutical agents make it a compound of considerable interest. The combination of the pyrrolidine ring with the nitrophenyl group provides a versatile structure for various chemical transformations and applications.