16112-59-7

Basic information

• Product Name: 2-Oxazolidinone, 4-methyl-
• Synonyms: 2-Oxazolidinone, 4-methyl-;4-Methyl-1,3-oxazolidin-2-one;4-Methyl-2-Oxazolidinone;4-methyloxazolidin-2-one
• CAS NO: 16112-59-7
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.10388
• Mol File: 16112-59-7.mol

Chemical Properties

• Melting Point: 56-57 °C
• Boiling Point: 266.2°Cat760mmHg
• Flash Point: 114.8°C
• Appearance: /
• Density: 1.157g/cm³
• PKA: 12.84±0.40(Predicted)
• CAS DataBase Reference: 2-Oxazolidinone, 4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 4-methyl-(16112-59-7)
• EPA Substance Registry System: 2-Oxazolidinone, 4-methyl-(16112-59-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 16112-59-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Oxazolidinone, 4-methylis used as a chemical intermediate for the synthesis of polyunsaturated fatty acid amides. These amides exhibit anti-proliferative properties, which can be beneficial in the development of pharmaceuticals targeting the inhibition of cell proliferation in various diseases, including cancer.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Oxazolidinone, 4-methylserves as a valuable building block for the creation of more complex molecules and compounds. Its unique structure allows for further functionalization and modification, making it a useful component in the synthesis of various organic compounds with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique properties and potential applications, 2-Oxazolidinone, 4-methylis also utilized in research and development settings. Scientists and researchers can use this compound to explore new chemical reactions, develop novel synthetic methods, and investigate its potential applications in various fields, including material science, drug discovery, and chemical engineering.

Upstream product

• 75-44-5 phosgene 
• 6168-72-5 2-Amino-1-propanol 
• 105-58-8 Diethyl carbonate 
• 14441-94-2 4-methoxy-1,3-oxazolidin-2-one 
• 75-16-1 methylmagnesium bromide 
• 84765-24-2 (S)-O-(p-tolylsulfonyl)-N-(tert-butyloxycarbonyl)-1-hydroxy-2-aminopropane 
• 86106-95-8 N-methoxycarbonylaziridine-2-carboxylic acid methyl ester 
• 170701-87-8 L-1-Benzyloxycarbonylaziridine-2-carboxylic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 
• 75-55-8 2-Methylaziridine 
• 616-38-6 carbonic acid dimethyl ester 
• 28875-17-4 (S)-N-(tert-butoxycarbonyl)alanine methyl ester 
• 57-13-6 urea 

Downstream Products

• 69047-40-1 N-phenyl-2-(thiophen-2-yl)acetamide 
• 1352448-50-0 methyl 2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoate 

Relevant articles and documents

Ceria nanoparticles as heterogeneous catalyst for CO2 fixation by ω-aminoalcohols

In contrast to γ-Al2O3, TiO2, ZrO2, MgO and Y2O3, CeO2 is a reusable catalyst for the reaction of CO2 with ω-aminoalcohols to form cyclic carbamates; the highest yield (68%) was obtained for the preparation of N-alkyl 1,3-oxazolidin-2-ones from N-alkyl ethanolamines.

Microwave assisted synthesis of fragrant jasmone heterocyclic analogues

cis-Jasmone, from jasmonoid group, is an important jasmine odor fragrance compound. The syntheses of new heterocyclic analogues of jasmone were described. Five analogues of this compound were prepared under microwave irradiation and the results of the microwave assisted syntheses were compared with classical, thermally initiated reactions in solvent. Microwave reactions were carried out successfully, and reaction times were significantly reduced to a few minutes. Three of five obtained analogues, pyrrolidinone, oxazolidinone and thiazolidinone demonstrated an interesting, specific odor which was compared with floral, typical jasmine odor of jasmone.

Microwave assisted synthesis of unsaturated jasmone heterocyclic analogues as new fragrant substances

Taking the rising interest in jasmone structure based fragrant compounds into account it has been decided to take up an attempt to synthesize the new heterocyclic derivatives of this 2,3-disubstituted cyclopentenone, which could be characterized by the ability of interaction with the same receptors with which jasmone affects. Obtained structures of unsaturated heterocyclic derivatives are based on pyrrolidinone, oxazolidinone, pyrazolidinone, pyrazolone and thiazolidinone systems with 2-double or 2-triple unsaturated five-carbon side chain. The rapid, highly yielding and ecofriendly microwave assisted organic syntheses (MAOS) have been used to obtain compounds mentioned above. Odor evaluation and relationships between their structure and osmic properties for all synthesized fragrant compounds have been studied. It has been shown that the majority of the obtained compounds have exhibited interesting, very intensive and fixative fragrant properties.

Effective scCO2-ionic liquid reaction system based on symmetric aliphatic ammonium salts for the rapid CO2 fixation with aziridine to 2-oxazolidinone

The hybrid reaction system composed of supercritical carbon dioxide and room temperature ionic liquid based on symmetric tetraalkyl ammonium salts can effectively promote the carbon dioxide fixation from aziridine to 2-oxazolidinone in the presence of iod

A sustainable protocol for the facile synthesis of zinc-glutamate MOF: An efficient catalyst for room temperature CO2 fixation reactions under wet conditions

A water stable zinc-MOF (ZnGlu) catalyst was facilely prepared from the proteinogenic amino acid, l-glutamic acid at room temperature in aqueous medium. CO2 fixations were promoted by the ZnGlu catalyst's inherently coordinated water and externally added water in yielding cyclic carbonate and cyclic urethane at room temperature. This eliminates the need for catalyst activation, making ZnGlu a ready-to-use catalyst. The enhanced CO2 cycloaddition with added water hints at the application of ZnGlu in wet flue gas conversions. This is the first reported attempt for the use of an MOF in the cycloaddition of aziridine and CO2.

SBA-15 Supported Dendritic ILs as a Green Catalysts for Synthesis of 2-Imidazolidinone from Ethylenediamine and Carbon Dioxide

In this work, a simple and facile approach is conducted for preparing many new SBA-15 supported dendritic imidazolium ILs heterogeneous catalysts SBA-15/IL(1–3) having high ionic density from SBA-15. SBA-15/IL(3) as a green heterogeneous catalyst can be used for synthesis of 2-imidazolidinone from ethylenediamine and carbon dioxide and considering solvent-free condition. SBA-15/IL(3) showed to have the highest catalytic activity besides a positive dendritic influence on the yields of the synthesis of 2-imidazolidinone in the presence of CO2 is seen because of existing the high-density peripheral zwitterionic ionic liquid functional groups on the biobased SBA-15/IL(3) catalyst surfaces. Graphical Abstract: [Figure not available: see fulltext.]

Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides

N,N′-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) was found to be an apposite promoter for the Cu-catalyzed N-arylation of oxazolidinones and primary and secondary amides with (hetero)aryl iodides at room temperature. Excellent chemoselectivity reached between

Ionic liquids/ZnO nanoparticles as recyclable catalyst for polycarbonate depolymerization

A useful protocol for waste bis-phenol A-polycarbonates (BPA-PC) chemical recycling is proposed based on a bifunctional acid/basic catalyst composed by nanostructured zinc oxide and tetrabutylammonium chloride (ZnO-NPs/NBu4Cl) in quality of Lewis acid and base, respectively. Retro-polymerization reaction proved to be of general application for several nucleophiles, including water, alcohols, amines, polyols, aminols and polyamines, leading to the complete recovery of BPA monomer and enabling the PC polymer to function as a green carbonylating agent (green phosgene alternative) for preparing carbonates, urethanes and ureas. A complete depolymerization can be obtained in seven hours at 100 °C and ZnO nanocatalyst can be recycled several times without sensible loss of activity. Remarkably, when polycarbonate is reacted with glycerol, it is possible to realize in a single process the conversion of two industrial wastes (BPA-PC and glycerol) into two valuable chemicals like BPA monomer and glycerol carbonate (the latter being a useful industrial solvent and fuel additive).

Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2-Oxazolidinones, and Benzoxazolones

The direct syntheses of ureas, oxamides, 2-oxazolidinones, and benzoxazolones by the oxidative carbonylation of amines, β-amino alcohols, and 2-aminophenols allows us to obtain high value added molecules, which have a large number of important applications in several fields, from very simple building blocks. We have found that it is possible to perform these transformations using the PdI2/KI catalytic system in an ionic liquid, such as 1-butyl-3-methylimidazolium tetrafluoroborate, as the solvent, the solvent/catalyst system can be recycled several times with only a slight loss of activity, and the product can be recovered easily by crystallization.

Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates

Copper(II) chloride catalyses the oxidative carbonylation of aminols, amine and alcohols to give 2-oxazolidinones, ureas and carbamates. Reaction proceeds smoothly in water under homogeneous conditions (Ptot = 4 MPa; PO2 = 0.6 MPa, PCO), at 100°C in relatively short reaction times (4 h) and without using bases or any other additives. This methodology represents an economic and environmentally benign non-phosgene alternative for the preparation of these three important N-containing carbonyl compounds.