N-[(4-Nitrophenyl)-methylsulfonyl]pyryolidine
[CAS# 340041-91-0]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Pyrroles
• Name: N-[(4-Nitrophenyl)-methylsulfonyl]pyryolidine
• Synonyms: 1-[[(4-Nitrophenyl)methyl]sulfonyl]-pyrrolidine
• Molecular Formula: C₁₁H₁₄N₂O₄S
• Molecular Weight: 270.30
• CAS Registry Number: 340041-91-0
• EC Number: 608-939-3
• SMILES: C1CCN(C1)S(=O)(=O)CC2=CC=C(C=C2)[N+](=O)[O-]

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 461.3±47.0 °C 760 mmHg (Calc.)^*
• Flash point: 232.8±29.3 °C (Calc.)^*
• Index of refraction: 1.612 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+351+338

Discovery and Applications

N-[(4-Nitrophenyl)-methylsulfonyl]pyrrolidine is an organic compound consisting of a pyrrolidine ring connected via a methylsulfonyl linker to a 4-nitrophenyl group. The structure features a five-membered saturated nitrogen-containing heterocycle (pyrrolidine) bonded through a sulfonyl (-SO₂-) group to a benzene ring substituted with a nitro (-NO₂) group at the para position.

This compound belongs to the class of sulfonamides, which are notable for their chemical stability and utility as intermediates in synthetic organic chemistry, especially in pharmaceutical and agrochemical development. The presence of the electron-withdrawing nitro group on the aromatic ring significantly influences the compound’s electronic properties, potentially affecting reactivity and biological activity.

The synthesis of N-[(4-nitrophenyl)-methylsulfonyl]pyrrolidine is generally achieved by reacting 4-nitrobenzenemethanesulfonyl chloride with pyrrolidine under controlled conditions. The sulfonyl chloride acts as an electrophile and undergoes nucleophilic substitution with the pyrrolidine nitrogen, forming the sulfonamide linkage. The reaction is typically performed in the presence of a base to neutralize the hydrogen chloride generated during the process.

Applications of this compound primarily lie in its role as a synthetic intermediate. The nitro substituent can be further transformed via reduction to an amino group or participate in other functional group modifications, enabling the synthesis of a wide variety of biologically active molecules. Such derivatives may exhibit activities including antimicrobial, anti-inflammatory, or enzyme inhibitory effects.

Chemically, the sulfonamide functionality confers high stability and participates in hydrogen bonding, which influences the compound’s solubility and solid-state properties. The pyrrolidine ring provides conformational rigidity and enhances lipophilicity, which can impact pharmacokinetic behavior when used in drug design.

Physicochemical properties of N-[(4-nitrophenyl)-methylsulfonyl]pyrrolidine include moderate polarity and expected solubility in polar organic solvents such as dimethylformamide, dimethyl sulfoxide, and methanol. It is generally a crystalline solid at room temperature.

Analytical characterization involves techniques such as nuclear magnetic resonance (NMR) spectroscopy, which confirms the chemical environment of protons and carbons within the molecule, infrared (IR) spectroscopy, which shows characteristic absorption bands for sulfonyl groups and nitro functionalities, and mass spectrometry for molecular weight verification.

In summary, N-[(4-nitrophenyl)-methylsulfonyl]pyrrolidine is a sulfonamide compound featuring a pyrrolidine moiety linked to a para-nitrophenyl group through a methylsulfonyl bridge. It serves as a valuable intermediate in organic synthesis with potential for further chemical transformations and applications in pharmaceutical research.

References

none