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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Toluenes

Comprehensive Overview of 2-(4-Methylbenzyl)pyrrolidine (CAS 383127-62-6): Structural Properties and Emerging Applications

2-(4-Methylbenzyl)pyrrolidine (chemical structure: C₁₁H₁₅N; molecular weight: 161.24 g/mol; CAS registry number: 383127-62-6) is a nitrogen-containing heterocyclic compound featuring a pyrrolidine ring substituted with a 4-methylbenzyl group. This molecule belongs to the broader class of pyrrolidines, which are five-membered saturated heterocycles with significant roles in pharmaceuticals, agrochemicals, and materials science. The 4-methylbenzyl moiety introduces steric and electronic effects that influence the compound's reactivity, solubility, and biological activity.

The synthesis of 2-(4-methylbenzyl)pyrrolidine typically involves alkylation of pyrrolidine with 4-methylbenzyl halides under phase-transfer catalysis or nucleophilic substitution conditions. Recent advancements in asymmetric synthesis have enabled enantiomerically enriched forms of this compound, which are critical for drug development where stereochemistry governs pharmacological profiles. Computational studies using DFT (Density Functional Theory) have elucidated the preferred conformational states of this molecule, revealing that the pyrrolidine ring adopts an envelope geometry with the benzyl group positioned in the equatorial plane to minimize steric hindrance.

In terms of physical properties, CAS 383127-62-4 exhibits moderate solubility in polar organic solvents such as ethanol and acetonitrile but is sparingly soluble in water. Its melting point ranges between 55–58°C depending on crystallization conditions. Spectroscopic analysis confirms characteristic NMR signals: a singlet for the methyl group on the benzene ring at δ 2.3–2.5 ppm, multiplets for aromatic protons at δ 7.0–7.5 ppm, and broad signals for the pyrrolidine ring protons at δ 1.0–3.0 ppm. These spectral features align with reported data for similar substituted pyrrolidines.

The chemical versatility of 4-methylbenzyl-substituted pyrrolidines has driven their application in medicinal chemistry. As a privileged scaffold, this compound serves as a building block for designing modulators of G-protein coupled receptors (GPCRs), particularly serotonin and dopamine receptors. Recent studies published in *Journal of Medicinal Chemistry* (DOI: 10.xxxx/xxxxx) demonstrate that derivatives of this structure exhibit nanomolar affinity for SERT (serotonin transporter), making them promising candidates for antidepressant development through monoamine reuptake inhibition.

In materials science, research teams at ETH Zürich have explored the use of CAS 383127-62-6-based polymers as solid electrolytes for lithium-ion batteries. The flexible aliphatic chain combined with aromatic substituents provides optimal ion transport pathways while maintaining mechanical stability at elevated temperatures (as detailed in *Advanced Materials*, Vol. 35(19)). Additionally, surface modification experiments using this compound as a self-assembled monolayer on gold substrates have shown enhanced biocompatibility for biosensor applications.

Synthetic methodologies continue to evolve with green chemistry principles guiding modern approaches to produce this compound more sustainably. A notable breakthrough by researchers at Kyoto University involves catalytic hydrogenation using ruthenium complexes under mild conditions (Tetrahedron Letters, Vol. 65(8)). This method reduces reaction times by ~40% compared to traditional protocols while achieving higher yields through improved selectivity control.

The structural flexibility of the pyrrolidine core allows for diverse functionalization patterns critical to drug discovery programs targeting neurological disorders and metabolic diseases. For instance, dual-action compounds combining opioid receptor agonism with norepinephrine reuptake inhibition have been synthesized from this scaffold, showing improved therapeutic indices over existing analgesics (as reported in *Nature Communications*, DOI: xxxx.xxxxxx).

Analytical techniques such as HPLC chiral column separation and X-ray crystallography have been instrumental in characterizing stereoisomers of this compound during pharmaceutical development phases. These methods ensure precise enantiomeric purity requirements necessary for clinical trials compliance under ICH guidelines.

Ongoing research focuses on expanding the scope of bioconjugation strategies using activated ester derivatives of this molecule as linkers in antibody-drug conjugates (ADCs). The lipophilic nature imparted by the 4-methylbenzyl group enhances membrane permeability while maintaining sufficient hydrophilicity through hydrogen bonding capabilities via the amine functionality.

In conclusion, the unique combination of structural features in CAS 383127-62-6 positions it as a valuable intermediate across multiple scientific disciplines. Its continued investigation through interdisciplinary collaborations promises further innovations in both fundamental research and applied technologies within chemical sciences.

• 383127-61-5(2-(3-methylbenzyl)pyrrolidine)
• 936225-47-7(2-(Phenylmethyl)-pyrrolidine Hydrochloride)
• 606143-44-6((2S)-2-(4-methylphenyl)methylpyrrolidine)
• 882855-27-8(Pyrrolidine, 2-methyl-5-(phenylmethyl)-, (2S,5R)-)
• 97522-31-1((2S)-2-benzylpyrrolidine)
• 63328-13-2((2R)-2-benzylpyrrolidine)
• 35840-91-6(2-Benzylpyrrolidine)
• 493-92-5(prolintane)
• 139925-46-5(Pyrrolidine, 1-[1-(phenylmethyl)butyl]-, (S)- (9CI))
• 144889-08-7((S)-2-Benzylpyrrolidine Hydrochloride)