2-Pyrrolidin-1-Ylethanol: A Comprehensive Commentary

Historical Development

Chemists have followed 2-Pyrrolidin-1-ylethanol through decades of lab notebooks, patent filings, and refinements in synthetic methods. Its story begins in postwar chemical research, fuelled by rising demands from both the pharmaceutical and specialty chemical sectors. Early synthetic attempts focused on N-alkylation reactions of pyrrolidine with haloethanols under basic conditions. This discovery made headway in the 1960s and 70s, at a time when organic synthesis chased after intermediates suited for new drugs and advanced materials. Over time, industrial processes moved from exploratory small-batch setups to larger-scale production, optimizing yields and purity thanks to improvements in purification and reaction controls. Demand from the flavors, fragrances, and active ingredient segments gradually shaped the market, drawing more attention to safety records and process repeatability. Today's production lines grew from that legacy, blending old chemistry with newer green protocols and stricter regulatory compliance.

Product Overview

2-Pyrrolidin-1-ylethanol serves as a hard-working intermediate, often mentioned in stories of drug development, coatings chemistry, and specialty solvent production. Its versatility draws from both the alcohol and the amine groups, making it valuable where molecular scaffolds need fine-tuned polarity or specific reactivity. The molecule's structure—pyrrolidine tethered by an ethyl chain to a terminal hydroxyl—lets it fit neatly into a range of chemical transformations fielded by research and manufacturing labs. The chemical's appeal relies partly on this flexibility and partly on the growing need for customizable intermediates in a world that prizes unique molecules for targeted applications. The roll-out of new therapies and materials routinely sees 2-pyrrolidin-1-ylethanol as a featured player, not just as a derivative but as a building block shaping bigger and more complex products.

Physical & Chemical Properties

2-Pyrrolidin-1-ylethanol appears as a clear, colorless to pale yellow liquid at room temperature, with a weak amine-like odor that can linger if handled in a poorly ventilated space. It registers a boiling point in the 100–110°C range at reduced pressure and features significant water solubility, thanks to the hydrophilic character of the alcohol group. A molecular weight close to 115 g/mol makes it manageable in dense reaction mixtures, while its polarity and hydrogen bonding potential open the door for wide miscibility with a variety of organic solvents. The molecule features both nucleophilic amine and electrophilic alcohol regions, often inviting reactions with acids, anhydrides, alkylating agents, and other partners. The dual-reactive nature seldom goes unnoticed by chemical engineers, who look for intermediates that unlock downstream modifications without introducing unwanted complexity.

Technical Specifications & Labeling

Producers label commercial-grade 2-pyrrolidin-1-ylethanol with a high purity threshold, typically aiming above 98%. Analytical techniques include NMR, GC-MS, and IR spectroscopy to confirm both purity and identity, with specific reference to melting point (if solid at lower temperatures), refractive index, and water content. Each drum or bottle carries UN-compliant safety labeling referencing hazards, handling recommendations, and storage needs. UN numbers and GHS hazard pictograms reflect known irritancy and toxicity risks—especially for eyes and skin—and provide first aid directives that echo regulatory standards adopted across continents. Storage containers use HDPE or glass, clearly marked to withstand mildly basic amine vapors. Inventory systems in most facilities enter detailed batch numbers and manufacturing dates, keeping traceability on par with standards needed for regulated sectors like pharmaceuticals.

Preparation Method

Chemists favor the N-alkylation route, where pyrrolidine reacts with 2-chloroethanol (or similar haloethanols) under mild base, such as sodium carbonate. The reaction calls for careful temperature management in a dry solvent to curb byproduct formation. Extraction with non-polar solvents, followed by distillation under reduced pressure, raises product yields into industrially attractive ranges. Variations sidestep chlorinated substrates by reaching for ethylene oxide or other less hazardous ethylene donors, guided by a desire for fewer hazardous byproducts and less demanding waste disposal. Improvements over the years reduced unwanted polymerization and improved scalability, finding a balance between cost and safety. Some laboratories prefer catalytic hydrogenation pathways, starting from pyrrolidone derivatives, though these require added investment in catalyst recovery and reactor maintenance. No single synthesis dominates outright, but all demand precise execution and a close eye on both throughput and waste reduction.

Chemical Reactions & Modifications

2-Pyrrolidin-1-ylethanol opens up a world of chemical creativity with both its nucleophilic nitrogen and hydroxyl group. In pharmaceutical research, acylation and alkylation of the nitrogen yield new scaffolds for active molecules. The alcohol moiety gets converted into esters, ethers, or oxidized to yield aldehydes and acids—expanding the range of building blocks from a single starting point. Under strong acid catalysis, ring-closure and rearrangement pathways offer access to rare cyclic species, some of which get tested for medicinal or materials science potential. The molecule's susceptibility to both electrophilic and nucleophilic substitution turns it into a reliable probe for synthetic method development. Skilled chemists exploit this dual reactivity to build libraries of analogs in drug design, especially in search of improved pharmacokinetic traits or novel receptor ligands.

Synonyms & Product Names

In catalogs and research papers, 2-pyrrolidin-1-ylethanol wears many names: N-(2-Hydroxyethyl)pyrrolidine, 1-(2-Hydroxyethyl)pyrrolidine, and N-(β-Hydroxyethyl)pyrrolidine. Suppliers might refer to CAS Number 1723-99-1 or simply list it under "2-HE Pyrrolidine." Cross-referencing synonyms helps avoid miscommunication in procurement, especially where language differences or regional conventions complicate ordering. Product codes line up on safety data sheets and technical documents to streamline logistics, keeping inventory managers and lab techs in sync. Variant names sometimes highlight the functional group's positions (like hydroxyethyl-pyrrolidine), ensuring that synthetists know exactly what structure to expect on delivery.

Safety & Operational Standards

Working with 2-pyrrolidin-1-ylethanol calls for personal protective gear: gloves built to resist both solvents and mild bases, protective eyewear to block splashes, and well-ventilated hoods as standard equipment. Vapor and skin irritation risks show up in both lab and production environments, demanding induction and routine safety audits. Facilities store the compound away from oxidizers, acids, and ignition sources since both amines and alcohols can react vigorously under certain conditions. Labels reference regulatory guidelines from OSHA, REACH, and globally harmonized systems, helping to standardize the safe handling procedures wherever the material finds use. Emergency showers, spill kits, and MSDS binders stay within arm’s reach in every facility that takes worker and environmental safety seriously. Disposal routes follow local regulations for amine and alcohol waste, with solvent recycling added to minimize environmental impact.

Application Area

2-Pyrrolidin-1-ylethanol answers the call across a range of fields. In pharmaceuticals, medicinal chemists build drug candidates with enhanced solubility or improved receptor selectivity. Coatings engineers find value in its solubilizing power, blending it into formulations that need both flexibility and toughness. In analytical chemistry, its dual-functionality makes it ideal as a chiral auxiliary or as a linker in solid-phase synthesis. The fragrance industry borrows it for aroma raw materials, shaping new odor profiles with synthetic precision. The compound even crops up in surface modification of polymers, helping materials scientists tailor interface performance or compatibility with additives. Researchers value this chemical for precisely these reasons—its role as a flexible tool for building out both research models and final products.

Research & Development

Interest in 2-pyrrolidin-1-ylethanol remains high at research benches worldwide because its structure sits at the crossroads of amine and alcohol reactivity. Academic labs thrive on this feature, driving the push for novel synthetic techniques, catalyst systems, and green chemistry routes. Funding agencies support programs that seek to move away from hazardous starting materials, while corporate R&D groups test its derivatives for new roles as corrosion inhibitors, plasticizers, and pharmaceutical intermediates. Software-aided molecular modeling unlocks more sophisticated uses, mapping out possibilities in peptide synthesis and supramolecular assembly. Collaborative patents flow from these efforts, feeding both academic publications and commercial pipelines. The challenge lies in keeping innovation steady while monitoring for unexpected toxicities or reactivity issues at scale.

Toxicity Research

Toxicologists keep a close watch on pyrrolidine derivatives because systemic effects in mammals often pop up after prolonged or high-level exposure. Standard testing finds eye and skin irritation possible, especially in concentrated form or with repeated contact. Metabolic breakdown pathways in animal studies suggest moderate to low acute toxicity, though subtle nervous system effects sometimes surface after high-dose exposures. In vitro, the chemical interrupts cell membrane function at elevated concentrations, drawing caution for large-scale industrial handling. Environmental toxicity data show rapid biodegradation in aerobic soils and water, but aquatic species still protest at runoff levels above regulatory limits. Continued monitoring at both production and application sites ensures environmental compliance, and periodic updates to safety data sheets reflect any revelations from animal or cell-based tests.

Future Prospects

Rising demand for selective building blocks in both old and emerging sectors means 2-pyrrolidin-1-ylethanol will keep earning its spot in catalogues and research feeds. Synthetic chemists continue digging for greener preparation methods, aiming to cut hazardous waste and energy bills. Application prospects depend heavily on further findings from toxicity research and regulatory reviews, especially in fields that touch human health and the environment. Ongoing collaborations between industry and academia promise a steady supply of new derivatizations, paving the way for better polymers, cleaner agrochemicals, and medicines with higher precision. In a global innovation race, the spotlight shines bright on compounds that bring both versatility and manageable risk, and this molecule delivers exactly that blend for now and the foreseeable future.




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2-Pyrrolidin-1-Ylethanol
2-Pyrrolidin-1-Ylethanol
2-Pyrrolidin-1-Ylethanol