N-tert-Butyl 4-Nitrophenylsulfonamide
[CAS# 49690-09-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: N-tert-Butyl 4-Nitrophenylsulfonamide
• Molecular Formula: C₁₀H₁₄N₂O₄S
• Molecular Weight: 258.29
• CAS Registry Number: 49690-09-7
• SMILES: CC(C)(C)NS(=O)(=O)C1=CC=C(C=C1)[N+](=O)[O-]

Safety Data

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

Discovery and Applications

N-tert-Butyl 4-Nitrophenylsulfonamide is a notable chemical compound with significant applications in both industrial chemistry and pharmaceutical research. This compound is an example of a sulfonamide derivative, which is known for its diverse chemical properties and biological activities.

The discovery of N-tert-Butyl 4-Nitrophenylsulfonamide emerged from research into sulfonamide compounds, which are characterized by the presence of a sulfonamide group attached to an aromatic ring. The specific structure of N-tert-Butyl 4-Nitrophenylsulfonamide features a tert-butyl group, which imparts increased steric bulk, and a nitrophenyl group, which introduces additional electronic effects due to the nitro group.

One of the key applications of N-tert-Butyl 4-Nitrophenylsulfonamide is in the field of pharmaceuticals. This compound is used as a reagent in the development of sulfonamide-based drugs. Sulfonamides are a class of compounds with antibacterial properties, and their derivatives are often used to develop new antibiotics. The nitrophenyl group in N-tert-Butyl 4-Nitrophenylsulfonamide can influence the biological activity of the molecule, making it a valuable tool for optimizing drug efficacy and selectivity.

In addition to its pharmaceutical applications, N-tert-Butyl 4-Nitrophenylsulfonamide is also employed in industrial chemistry. Its ability to act as a reactive intermediate in various chemical reactions makes it useful in the synthesis of other chemical compounds. For example, it can be used in the preparation of sulfonamide-containing polymers, which have applications in materials science due to their stability and chemical resistance.

The compound's distinctive structure, featuring the tert-butyl group and nitrophenyl group, contributes to its reactivity and utility. The tert-butyl group provides steric protection, preventing unwanted side reactions, while the nitro group can enhance the electronic properties of the molecule, influencing its interactions in chemical reactions.

Overall, N-tert-Butyl 4-Nitrophenylsulfonamide is a compound of significant interest due to its applications in drug development and industrial synthesis. Its unique chemical structure allows it to play a role in advancing both pharmaceutical research and materials science. As research continues, this compound may contribute to new discoveries and innovations in these fields.

References

2014. Silver(I) Oxide. Synlett, 25(16).
DOI: 10.1055/s-0034-1379002

2013. SNAAP Sulfonimidate Alkylating Agent for Acids, Alcohols, and Phenols. Synthesis, 45(22).
DOI: 10.1055/s-0033-1339921