N-[(4-Aminophenyl)-methylsulfonyl]pyryolidine
[CAS# 334981-10-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Pyrroles
• Name: N-[(4-Aminophenyl)-methylsulfonyl]pyryolidine
• Synonyms: 4-[(1-Pyrrolidinylsulfonyl)methyl]-benzenamine; 1-[[(4-Aminophenyl)methyl]sulfonyl]-pyrrolidine
• Molecular Formula: C₁₁H₁₆N₂O₂S
• Molecular Weight: 240.32
• CAS Registry Number: 334981-10-1
• EC Number: 608-876-1
• SMILES: C1CCN(C1)S(=O)(=O)CC2=CC=C(C=C2)N

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 434.2±47.0 °C 760 mmHg (Calc.)^*
• Flash point: 216.4±29.3 °C (Calc.)^*
• Index of refraction: 1.618 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

N-[(4-Aminophenyl)-methylsulfonyl]pyrrolidine is an organic compound characterized by a pyrrolidine ring attached via a methylsulfonyl linker to a 4-aminophenyl group. Structurally, it consists of a five-membered saturated nitrogen-containing heterocycle (pyrrolidine), which is connected through a sulfonyl (-SO₂-) functional group to a benzene ring bearing an amino (-NH₂) substituent at the para position.

This compound falls into the class of sulfonamides, which are known for their diverse applications in medicinal chemistry, materials science, and synthetic intermediates. The sulfonyl linkage imparts chemical stability and polarity to the molecule, while the amino group provides sites for further derivatization or interaction with biological targets.

The synthesis of N-[(4-aminophenyl)-methylsulfonyl]pyrrolidine typically involves the reaction of 4-aminobenzenemethanesulfonyl chloride with pyrrolidine under controlled conditions. The sulfonyl chloride acts as an electrophile, reacting with the nucleophilic nitrogen of the pyrrolidine to form the sulfonamide bond. This reaction generally proceeds smoothly in the presence of a base to neutralize the generated hydrochloric acid.

Applications of this compound are primarily as an intermediate in the synthesis of pharmaceuticals and agrochemicals. The structural features, including the sulfonamide moiety and the amine functionality, allow it to serve as a versatile building block in the design of molecules with biological activity such as enzyme inhibitors, antimicrobial agents, or receptor ligands.

Due to the presence of both nucleophilic and electrophilic sites, this compound can undergo various chemical transformations. For instance, the amino group on the aromatic ring can be modified through acylation, alkylation, or diazotization reactions, expanding the chemical diversity accessible from this scaffold. The pyrrolidine ring contributes to conformational rigidity and lipophilicity, influencing the compound's physicochemical properties.

Physicochemically, N-[(4-aminophenyl)-methylsulfonyl]pyrrolidine is expected to be a solid with moderate polarity, soluble in polar organic solvents such as dimethylformamide, dimethyl sulfoxide, or methanol. The sulfonamide group can participate in hydrogen bonding, affecting solubility and crystal packing.

Analytical characterization techniques commonly used for this compound include nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry. NMR data provide information on the chemical environment of protons and carbons, confirming the presence of the aromatic ring, sulfonamide linkage, and pyrrolidine moiety. IR spectroscopy shows characteristic absorptions for sulfonyl groups (around 1150–1350 cm^-1) and amine N–H stretches.

In conclusion, N-[(4-aminophenyl)-methylsulfonyl]pyrrolidine is a sulfonamide compound featuring a pyrrolidine ring linked to a para-aminophenyl group through a methylsulfonyl bridge. It serves as an important synthetic intermediate in medicinal chemistry with potential for diverse chemical modifications and applications.

References

2003. Almotriptan. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0073