Communities of chemists first took notice of piperidine rings in the 19th century, and the search for modifications began soon after. When ethanol branches attached themselves to this scaffold, a host of new molecules became possible, including 2-piperidin-2-ylethanol. At first, the tuning of this compound trailed behind more popular amine and alcohol derivatives. Academic research in the mid-20th century shifted, and interest in heterocyclic frameworks led to a spike in reported syntheses. Early records show researchers in medicinal chemistry labs tinkering with piperidine-based alcohols. This interest now continues, as industrial and research laboratories pursue new functionalities and sustainable syntheses, using 2-piperidin-2-ylethanol as a stepping stone.
2-Piperidin-2-ylethanol combines two functional elements: a secondary amine from the piperidine ring and a primary alcohol. Manufacturers most often supply it as a colorless to pale yellow liquid or solid, depending on purity and storage temperature. Researchers prize its reactivity, as the combination of alcohol and nitrogen in its backbone opens up diverse downstream chemical modifications. The compound is often used as an intermediate for pharmaceuticals, agrochemicals, and specialty catalysts. Its structure shapes its role in many chemical strategies, as few other molecules combine piperidine and hydroxyethyl so seamlessly.
The compound melts around room temperature, though the crystalline form sometimes requires careful chilling. The molecular weight hovers just below 130 g/mol, and the boiling point tends to fall between 230 and 240°C at standard pressure, which means you can purify it by careful distillation but risk decomposition if you rush the process. In terms of solubility, 2-piperidin-2-ylethanol dissolves readily in water and most organic solvents, thanks to its alcohol and amine groups. It behaves as a mild base due to the nitrogen atom, giving it moderate reactivity with acids and electrophiles. It does not react violently with air or water, but its basicity and alcohol function create opportunity for multiple downstream transformations.
Producers list 2-piperidin-2-ylethanol with CAS number 33486-14-9. Regulatory labeling typically details hazard warnings around skin and eye irritation, as well as possible environmental persistence. Purity for technical and research use often exceeds 98%. The SDS will describe measures for personal protection and engineered ventilation, and the label emphasizes the importance of proper storage, particularly excluding strong oxidizers or acids. Some suppliers polymerize impurities more slowly by using amber glass or nitrogen blankets for long-term storage, and larger containers bear secondary containment and spill instructions. Batch traceability marks and expiration dates assure users the material has not degraded.
Manufacturers commonly synthesize 2-piperidin-2-ylethanol through ring-closure reactions of appropriate amino-alcohols or by the reduction of keto intermediates. One approach combines 2-piperidinone with ethylene oxide under controlled alkaline conditions, creating high yields but demanding careful pH management and slow addition to avoid runaway reactions. Another route uses Grignard reagents or organolithiums to introduce the ethanol group onto activated piperidine rings, though handling these intermediates requires experience with air-sensitive chemistry. Reduction strategies start with piperidin-2-one and reduce it with hydride donors in alcohol solvents; this method is receptive to large-scale implementation. Across all routes, product purification by distillation or crystallization assures the quality needed for further synthetic steps.
Having a free alcohol and a secondary amine makes 2-piperidin-2-ylethanol versatile. Alkylation, acylation, and etherification typically modify the alcohol, adding bulk or adjusting polarity. Protection-deprotection strategies use silyl or benzyl groups to block either end, for selective functionalization. Researchers exploit the amine for reductive amination or to create amide linkages, particularly in pharmaceutical intermediate syntheses. Oxidation of the alcohol produces aldehydes or carboxylic acids, opening routes to even more functionalized substructures. Pairing these traits, the molecule can help build complex polycyclic compounds, or link multiple functional domains in bioactive agents or even polymer monomers.
In academic and commercial circles, you’ll find 2-piperidin-2-ylethanol also described as 2-(2-Hydroxyethyl)piperidine or simply piperidinylethanol. European and Asian catalogs might list it as 2-hydroxyethylpiperidine. Despite small naming differences, reference to CAS 33486-14-9 usually clears up confusion. Some chemical databases use older naming formats, such as β-hydroxyethylpiperidine, and misspellings abound due to the odd double “2” in its preferred IUPAC name. For product identification, cross-referencing with chemical structure and registry number remains best practice.
Labs and process plants treat 2-piperidin-2-ylethanol with the respect typical of low-volatility amines. Gloves and eye protection form the basic outfit, as the compound stings eyes and can cause dermatitis with repeated skin exposure. Ventilation proves essential, not just for handling dust or vapor but for air-sensitive reactions that involve strong bases or acids. Standard operating protocols call for quick cleanup of spills, absorption with inert media, and disposal as hazardous organic waste. Fire risk stays low, but in an emergency, CO2 or foam extinguishers take priority over water. Long-term stability depends on cool, dry storage and the exclusion of reactive materials. Occupational exposure limits are not tightly regulated, but prudent management minimizes handling time and ensures quick access to MSDS instructions.
Pharmaceutical development leads the demand, as 2-piperidin-2-ylethanol steps in as both a building block and a chain extender for more complex heterocycles. Its role in agrochemical synthesis comes close behind, where it helps create chiral ligands or pesticide intermediates. Synthetic chemists value it for the flexibility of its alcohol group; linker chemistry, functionalization, and development of bioactive molecules form the main pathways. In catalysis, the molecule sometimes anchors ligands to solid supports or modifies chelating backbones, increasing selectivity and process efficiency. While less common, it pops up in polymer chemistry as a monomer or additive, adjusting chain properties or hydrophilicity for advanced coatings and resins. Its compatibility with fine chemical production makes it a staple in pilot and bench-scale routes for new material synthesis.
Recent research on 2-piperidin-2-ylethanol explores bioactivity, chiral pool exploitation, and regioselective functionalization. Academic and industrial groups chase after efficient, green synthesis protocols to reduce energy and hazardous byproducts, including biocatalytic routes with whole cells or tailored enzymes. Some groups publish studies on asymmetric modifications to access enantiomerically pure forms for pharmaceuticals. Lab groups develop high-throughput screening routines, where the ethanol and piperidine moieties allow combinatorial methods for drug candidate libraries. Analytical research includes detailed NMR, mass spectrometry, and IR studies to track purity and map side product profiles, as impurities or stereoisomers can have significant downstream effects.
Published animal studies suggest mild to moderate toxicity profiles, typical of secondary amines and small alcohols. Acute exposure in rodents leads to irritant effects but rarely fatal poisoning, though repeated dosing does raise liver enzyme levels or mild neurotoxicity. No legitimate evidence yet links 2-piperidin-2-ylethanol to mutagenicity or carcinogenicity, but the field could benefit from more studies, especially with repeated low-dose exposures and bioaccumulation risks. Chemical safety committees require more granular chronic toxicity data before allowing wider use in consumer products. Waste management takes these risks seriously, ensuring destruction of the molecule before environmental release.
Interest in 2-piperidin-2-ylethanol looks set to grow, as its core structure fits with shifting trends in drug discovery, catalysis, and material science. Researchers look for sustainable syntheses, aiming for biobased feedstocks or enzymatic routes to cut out hazardous reagents and lower overall emissions. If greener production matures and costs drop, large-volume technical uses in polymer and coatings technology could open up. Regulatory landscapes change fast, so ongoing work on toxicology and environmental fate finds itself on the front lines, ensuring this molecule doesn’t get left out as greener alternatives rise. Continued innovation in selective functionalization will expand its toolkit for custom molecules, giving future chemists both options and insight.
