3356-88-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-Hydroxyethyl)-2-oxazolidinone is used as a solvent for its ability to dissolve a wide range of substances, which is crucial in the formulation of various pharmaceutical products. Its solubility capabilities make it particularly useful for topical and transdermal drug applications, enhancing the delivery and effectiveness of medications.
Used in the Synthesis of Pharmaceutical Compounds:
3-(2-Hydroxyethyl)-2-oxazolidinone is utilized as a reactant in the synthesis of new pharmaceutical compounds, contributing to the development of innovative treatments and therapies.
Used as a Chiral Auxiliary in Asymmetric Synthesis Reactions:
In the realm of asymmetric synthesis, 3-(2-Hydroxyethyl)-2-oxazolidinone serves as a chiral auxiliary, playing a critical role in enhancing the selectivity and yield of desired enantiomeric products, which is essential for the production of high-quality pharmaceuticals.
Used as a Green Alternative to Conventional Organic Solvents:
3-(2-Hydroxyethyl)-2-oxazolidinone is employed as an eco-friendly substitute for traditional organic solvents, reducing the environmental impact of chemical processes due to its low toxicity and biodegradability. This makes it a preferred choice in industries striving for sustainable practices.

InChI:InChI=1/C5H9NO3/c7-3-1-6-2-4-9-5(6)8/h7H,1-4H2

Upstream product

• 124-38-9 carbon dioxide 
• 111-42-2 2,2'-iminobis[ethanol] 
• 107-21-1 ethylene glycol 
• 57-13-6 urea 
• 115-19-5 2-methyl-but-3-yn-2-ol 

Downstream Products

• 2508-01-2 3-(2-chloroethyl)-2-oxazolidinone 
• 159974-55-7 4-methylbenzenesulfonic acid-2-(2-oxazolidinone-3-yl)ethyl ester 
• 1075700-90-1 2-fluoro-5-{2,3-difluoro-6-[2-(oxazolidin-2-one-3-yl)ethoxy]benzyloxy}aniline 
• 115965-75-8 acrylic acid 2-(2-oxo-oxazolidin-3-yl)-ethyl ester 
• 89869-36-3 3-(2-bromoethyl)oxazolidin-2-one 
• 122-96-3 1,4-bis(2-hydroxyethyl)piperazine 
• 1386394-49-5 4-nitrophenyl (2-(2-oxooxazolidin-3-yl)ethyl)carbonate 
• 1386394-74-6 C₂₈H₃₆N₄O₇S₂ 
• 1386394-69-9 C₂₈H₃₉N₃O₈S 
• 1386394-60-0 2-(2-oxooxazolidin-3-yl)ethyl ((2S,3R)-3-hydroxy-4-(4-methoxy-N-((S)-2-methylbutyl)phenylsulfonamido)-1-phenylbutan-2-yl)carbamate 
• 75125-23-4 (2-oxo-1,3-oxazolidin-3-yl)acetic acid 
• 59849-49-9 (-)-(R)-3-<2-<4-(8-Fluor-10,11-dihydro-2-methyldibenzo thiepin-10-yl)-1-piperazinyl>-aethyl>-2-oxazolidinon 
• 52548-37-5 3-[2-(4-benzyl-piperazin-1-yl)-ethyl]-oxazolidin-2-one 
• 159974-46-6 3-(2-Cyclohexylamino-ethyl)-oxazolidin-2-one 

Relevant academic research and scientific papers

An efficient and recyclable AgNO3/ionic liquid system catalyzed atmospheric CO2 utilization: Simultaneous synthesis of 2-oxazolidinones and α-hydroxyl ketones

Oxazolidinones and α-hydroxyl ketones are two series of fine chemicals that have been generally utilized in biological, pharmaceutical, and synthetic chemistry. Herein, a AgNO3/ionic liquid (IL) catalytic system was developed for the simultaneous synthesis of these compounds through the atom-economical three-component reactions of propargyl alcohols, 2-aminoethanols, and CO2. Notably, this system behaved excellent catalytic activity with the lowermost metal loading of 0.25 mol%. Meanwhile, it is the first reported metal-catalyzed system that could efficiently work under atmospheric CO2 pressure and be recycled at least five times. Evaluation of the green metrics proved the AgNO3/IL-catalyzed processes to be relatively more sustainable and greener than the other Ag-catalyzed examples. Further mechanistic investigations revealed the derivative active species of N-heterocyclic carbene (NHC) silver complexes and CO2 adducts generated during the process. Subsequently, their reactivity in this reaction was assessed for the first time, which was finally identified as beneficial for the catalytic activity.

Highly synergistic effect of ionic liquids and Zn-based catalysts for synthesis of cyclic carbonates from urea and diols

The development of stable and efficient catalysts is an attractive topic for green chemistry reactions under mild reaction conditions. In order to improve solvent-free synthesis of cyclic carbonates from urea and diols, a binary catalyst systems of Zn-based and different ionic liquids (ILs) were developed and examined in this study. The yield of ethylene carbonate (EC) could reach to 92.2% in the presence of C16mimCl/ZnCl2 catalyst. Through exploring the structure-activity relationships of cation and anion, it was confirmed that a synergistic effect of cation and anion of catalyst had important influences on urea alcoholysis. Additionally, the controlling step of EC synthesis reaction involving the elimination of an ammonia molecule from intermediates had been revealed by in situ FT-IR. This could afford a guided insight for synthesizing cyclic carbonates with high yield. Furthermore, a possible mechanism for the catalytic process was proposed based on DFT and the experimental results via FT-IR, 1H-NMR and 13C NMR analysis, which revealed that not only a probable synergistic effects of cation-anion matters, but also C(2)-H of ILs and Zn2+ played a key role in accelerating the reaction of urea alcoholysis. This catalytic mechanism study is to provide a preliminary basis to develop novel catalysts for cyclic carbonates from urea and diols through a green synthetic pathway.

Continuous N-alkylation reactions of amino alcohols using γ-Al2O3 and supercritical CO2: Unexpected formation of cyclic ureas and urethanes by reaction with CO2

The use of γ-Al2O3 as a heterogeneous catalyst in scCO2 has been successfully applied to the amination of alcohols for the synthesis of N-alkylated heterocycles. The optimal reaction conditions (temperature and substrate flow rate) were determined using an automated self-optimising reactor, resulting in moderate to high yields of the target products. Carrying out the reaction in scCO2 was shown to be beneficial, as higher yields were obtained in the presence of CO2 than in its absence. A surprising discovery is that, in addition to cyclic amines, cyclic ureas and urethanes could be synthesised by incorporation of CO2 from the supercritical solvent into the product.

AgI/TMG-Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2-Aminoethanols to 2-Oxazolidinones

Chemical valorization of CO2 to access various value-added compounds has been a long-term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one-pot three-component reaction of terminal propargyl alcohols, CO2, and 2-aminoethanols was developed for the synthesis of 2-oxazolidinones and an equal amount of α-hydroxyl ketones promoted by Ag2O/TMG (1,1,3,3-tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2-aminoethanol/CO2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2-aminoethanol through the formation of hydrogen bonds and also activate CO2.

Thermodynamically favorable synthesis of 2-oxazolidinones through silver-catalyzed reaction of propargylic alcohols, CO2, and 2-aminoethanols

Development of catalytic routes to incorporate CO2 into carbonyl compounds at mild conditions remains attractive and challenging. Herein, a one-pot three-component cascade reaction of terminal propargylic alcohols, CO2, and 2-aminoethanols through AgI-based catalysis is reported for the synthesis of carbonyl compounds through C—O/C—N bond formation. This thermodynamically favorable route can be ingeniously regulated to afford a wide range of 2-oxazolidinones along with concurrent production of α-hydroxyl ketone derivatives in excellent yields and selectivity. Preliminary mechanistic studies indicate that such a process proceeds through successive formation of α-alkylidene cyclic carbonate, β-oxopropylcarbamate, and 2-oxazolidinones.