N,N-Diethyl-2-nitroaniline
[CAS# 2216-17-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: N,N-Diethyl-2-nitroaniline
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.23
• CAS Registry Number: 2216-17-3
• SMILES: CCN(CC)C1=CC=CC=C1[N+](=O)[O-]

Discovery and Applications

N,N-Diethyl-2-nitroaniline is an important chemical compound in organic synthesis, recognized for its unique properties and diverse applications. This compound features a nitro group and an aniline ring, with two ethyl groups attached to the nitrogen atom, making it a significant substance in both research and industrial contexts.

The discovery of N,N-diethyl-2-nitroaniline dates back to the exploration of nitroaniline derivatives, which are known for their utility in various chemical reactions. The introduction of ethyl groups to the nitrogen enhances the compound's solubility and stability, making it a valuable building block in synthetic chemistry.

One of the primary applications of N,N-diethyl-2-nitroaniline is as a precursor in the synthesis of dyes and pigments. The nitroaniline structure is integral to many colorants, and the ethyl substitution can modify the electronic properties of the molecule, leading to different hues and stability. This makes N,N-diethyl-2-nitroaniline a useful intermediate in the production of specialty dyes used in textiles, plastics, and other materials.

In addition to its role in dye synthesis, N,N-diethyl-2-nitroaniline is employed in various organic transformations. The compound is used as a reagent in chemical reactions, including those that form new carbon-nitrogen bonds. Its reactivity and stability make it a suitable choice for diverse synthetic pathways, contributing to the development of new pharmaceuticals, agrochemicals, and materials.

The compound is also of interest in the field of chemical research due to its ability to participate in reactions such as reductions and couplings. These reactions are essential for creating complex molecules with specific properties, making N,N-diethyl-2-nitroaniline a valuable tool for chemists working on novel compounds and materials.

Overall, N,N-diethyl-2-nitroaniline represents an important component in organic chemistry with a range of applications from dye synthesis to chemical research. Its properties and versatility highlight its significance in both industrial and academic settings.

References

1964. Gasometric determination of nitrogen in organic substances Communication 3. New rapid method of determining nitrogen. *Bulletin of the Academy of Sciences of the USSR, Division of chemical science*, 13(9).
DOI: 10.1007/bf00846275