N-tert-Butyl-4-aminobenzenesulfonamide
[CAS# 209917-48-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: N-tert-Butyl-4-aminobenzenesulfonamide
• Molecular Formula: C₁₀H₁₆N₂O₂S
• Molecular Weight: 228.31
• CAS Registry Number: 209917-48-6
• EC Number: 687-656-7
• SMILES: CC(C)(C)NS(=O)(=O)C1=CC=C(C=C1)N

Properties

• Solubility: Slightly soluble (1.4 g/L) (25 °C), Calc.^*
• Density: 1.189±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

N-tert-Butyl-4-aminobenzenesulfonamide, commonly known as a sulfonamide derivative, is an organic compound with notable significance in both chemical synthesis and pharmaceutical applications. This compound is characterized by its sulfonamide group, an amine group, and a tert-butyl group attached to a benzene ring, making it a versatile substance in various chemical processes.

The discovery of N-tert-butyl-4-aminobenzenesulfonamide is part of the broader exploration of sulfonamide derivatives, which began in the early 20th century. Sulfonamides were first introduced as antibiotics in the 1930s, following the groundbreaking work of Gerhard Domagk and colleagues. They discovered that sulfonamides could effectively inhibit bacterial growth by interfering with folic acid synthesis, a critical process for bacterial survival. While the specific derivative N-tert-butyl-4-aminobenzenesulfonamide was developed later, it inherits the important properties of sulfonamides and extends their utility.

One of the primary applications of N-tert-butyl-4-aminobenzenesulfonamide is in pharmaceutical development. This compound serves as an intermediate in the synthesis of various drugs, particularly those targeting bacterial infections and other medical conditions. Its structure allows for the introduction of additional functional groups, facilitating the creation of complex molecules required for effective therapeutics. By modifying the sulfonamide group or the amine group, researchers can develop new drugs with enhanced efficacy or reduced side effects.

In addition to its role in drug synthesis, N-tert-butyl-4-aminobenzenesulfonamide has applications in biochemical research. It is used as a reagent in various chemical assays and studies, particularly those focusing on enzyme inhibition and protein interactions. The compound’s sulfonamide group can interact with enzymes, providing insights into enzyme mechanisms and helping in the design of new inhibitors.

The compound also finds use in materials science. The sulfonamide group and the tert-butyl group can be incorporated into polymers and other materials to modify their properties. For example, these modifications can enhance the thermal stability or solubility of the materials, making them suitable for specific applications in coatings, adhesives, or advanced materials.

In summary, N-tert-butyl-4-aminobenzenesulfonamide is a versatile compound with significant applications in pharmaceuticals, biochemical research, and materials science. Its discovery builds upon the foundational work of sulfonamides, and its unique structure enables its use in various chemical processes. From drug development to materials modification, this compound continues to play a valuable role in advancing both scientific research and industrial applications.

References

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