1-(4-Nitrophenyl)-1H-pyrazole
[CAS# 3463-30-7]

Identification

• Name: 1-(4-Nitrophenyl)-1H-pyrazole
• Molecular Formula: C₉H₇N₃O₂
• Molecular Weight: 189.17
• CAS Registry Number: 3463-30-7
• SMILES: C1=CN(N=C1)C2=CC=C(C=C2)[N+](=O)[O-]

Safety Data

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

Discovery and Applications

1-(4-Nitrophenyl)-1H-pyrazole is an organic compound that features a pyrazole ring substituted with a nitrophenyl group. Its distinctive structure, combining a pyrazole core with a nitro group attached to a phenyl ring, makes it a notable compound in various fields, including medicinal chemistry and material science.

The discovery of 1-(4-Nitrophenyl)-1H-pyrazole is rooted in the study of pyrazole derivatives, which are known for their diverse biological and chemical properties. Pyrazole itself is a five-membered ring containing two adjacent nitrogen atoms, which makes it a versatile building block in organic synthesis. The introduction of a nitrophenyl group at the 1-position of the pyrazole ring imparts additional functionality, influencing the compound's chemical reactivity and potential applications.

The synthesis of 1-(4-Nitrophenyl)-1H-pyrazole typically involves the reaction of a suitable 4-nitrophenyl hydrazone with an appropriate aldehyde or ketone under acidic or basic conditions. The reaction conditions, including solvent choice, temperature, and reaction time, are optimized to achieve high yield and purity. Purification methods such as recrystallization or column chromatography are used to isolate the final product, which is then characterized by techniques such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.

One of the primary applications of 1-(4-Nitrophenyl)-1H-pyrazole is in medicinal chemistry. The compound's structure makes it a valuable intermediate in the synthesis of pharmaceuticals. Its ability to act as a ligand or to participate in further chemical reactions enables the development of new drugs with specific biological activities. For instance, derivatives of 1-(4-Nitrophenyl)-1H-pyrazole have been explored for their potential as anti-inflammatory, anti-cancer, or antimicrobial agents. The nitro group, in particular, can influence the biological activity of the compound, making it a useful component in drug design.

In addition to its role in medicinal chemistry, 1-(4-Nitrophenyl)-1H-pyrazole finds applications in material science. The compound's chemical properties allow it to be used in the development of new materials with specific optical or electronic characteristics. For example, it can be incorporated into organic semiconductors or light-emitting materials, where its presence can enhance the performance of the final product. The nitrophenyl group can also influence the electronic properties of the pyrazole ring, leading to materials with tailored properties.

Another significant application of 1-(4-Nitrophenyl)-1H-pyrazole is in chemical research as a reagent or probe. Its ability to participate in various chemical reactions and its distinctive absorbance properties make it useful for studying reaction mechanisms or for probing chemical environments. The compound's reactivity and the presence of the nitro group provide opportunities for exploring new reactions or for developing new analytical techniques.

Despite its advantages, challenges associated with 1-(4-Nitrophenyl)-1H-pyrazole include optimizing its synthesis to improve yield and purity, as well as exploring its full range of applications. Ongoing research aims to address these challenges and to expand the compound's utility in different fields.

Future research into 1-(4-Nitrophenyl)-1H-pyrazole may focus on developing new derivatives with enhanced properties or exploring its potential in emerging technologies. Its unique structure and reactivity offer opportunities for innovation in both medicinal chemistry and material science, contributing to advancements in these areas.

References

2018. Synthesis of Pyrazole derivatives. Journal of Heterocyclic Chemistry, 55(7).
DOI: 10.1002/jhet.3198