1072-70-4

Basic information

• Product Name: 5-Methyloxazolidin-2-one
• Synonyms: 5-Methyloxazolidin-2-one;5-Methyl-2-oxazolidinone;5-Methyl-1,3-oxazolidin-2-one
• CAS NO: 1072-70-4
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.11
• Mol File: 1072-70-4.mol
• Article Data: 36

Chemical Properties

• Melting Point: 20-22 °C
• Boiling Point: 302.6°Cat760mmHg
• Flash Point: 136.8°C
• Appearance: /
• Density: 1.095g/cm³
• Vapor Pressure: 0.000981mmHg at 25°C
• Refractive Index: 1.425
• PKA: 12.82±0.40(Predicted)
• CAS DataBase Reference: 5-Methyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyloxazolidin-2-one(1072-70-4)
• EPA Substance Registry System: 5-Methyloxazolidin-2-one(1072-70-4)

Safety Data

• Hazardous Substances Data: 1072-70-4(Hazardous Substances Data)

Usage

General Description

5-Methyloxazolidin-2-one is a chemical compound with the molecular formula C4H7NO2. It is a cyclic organic compound belonging to the oxazolidinone family. 5-Methyloxazolidin-2-one is a colorless, crystalline solid with a characteristic odor. 5-Methyloxazolidin-2-one is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals due to its versatile reactivity and high stability. It is also known for its potential applications in asymmetric synthesis and as a chiral auxiliary in organic chemistry. Furthermore, this compound has been investigated for its antimicrobial and antifungal properties, making it a promising candidate for the development of new drugs and biologically active molecules.

InChI:InChI=1/C4H7NO2/c1-3-2-5-4(6)7-3/h3H,2H2,1H3,(H,5,6)

Upstream product

• 75-44-5 phosgene 
• 38033-42-0 1-trimethylsilanylamino-2-trimethylsilanyloxy-propane 
• 75161-78-3 1-methyl-2-bromoethyl N-acetylcarbamate 
• 1659-31-0 2,2'-dipyridyl carbonate 
• 78-96-6 3-amino-2-propanol 
• 108-80-5 isocyanuric acid 
• 75-56-9 methyloxirane 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 
• 75-55-8 2-Methylaziridine 
• 598-55-0 methyl carbamate 
• 51-79-6 urethane 
• 592-35-8 butyl carbamate 
• 57-13-6 urea 

Downstream Products

• 5467-84-5 1,3-diphenethylurea 
• 78-96-6 3-amino-2-propanol 
• 3395-98-0 5-methyl-3-vinyloxazolidin-2-one 
• 107150-05-0 4-(5-methyl-2-oxo-oxazolidin-3-yl)-benzoic acid ethyl ester 
• 7007-16-1 3-benzoyl-5-methyl-1,3-oxazolidin-2-one 
• 133365-68-1 5-methyl-3-phenoxycarbonyl-2-oxazolidone 
• 4293-57-6 N-(2-hydroxypropyl)-acetamide 

Relevant articles and documents

PREPARATION OF CYCLIC CARBONATES AND 2-OXAZOLIDONES USING DI-2-PYRIDYL CARBONATE

Cyclic carbonates and 2-oxazolidones are conveniently prepared in high yields by the reaction of diols and β-amino alcohols with di-2-pyridyl carbonate.It is of synthetic significance that the formation of cyclic carbonates in refluxing toluene occurs under essentially neutral conditions.

Synthesis of 2-oxazolidinones from CO2 and 1,2-aminoalcohols catalyzed by n-Bu2SnO

The dehydrative condensation of 1,2-aminoalcohols with CO2 is found to proceed in NMP as solvent; 2-oxazolidinones are obtained in the yields of 53-94% when a commercially available tin compound, n-Bu2SnO is used as catalyst.

Novel α-aminophosphonic acids. Design, characterization, and biological activity

Novel α-aminophosphonic acids are synthesized reacting 1,3-oxazolidin-2-one derivatives with formaldehyde and phosphorus trichloride. Treatment of N-(phosphonomethyl)oxazolidinones with aqueous NaOH gave the expected α-aminophosphonic acids. The oxidation

Pd(Phen)Cl2 stabilized by ionic liquid: an efficient and reusable catalyst for biphasic oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol

Biphasic oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol to synthesize corresponding 2-oxazolidinones were investigated in the presence of ionic liquid stabilized Pd(phen)Cl2 complex. Catalytic comparison results showed that, 1-butyl-3-methyl-imidazolium iodide salts (BMImI) can serve simultaneously as a specific stabilizer to protect the transition metal complex against deactivation, a promoter to increase the catalytic performance and a reaction medium to recycle the catalyst with unprecedented TOF value.

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.]

Efficient route for oxazolidinone synthesis using heterogeneous biopolymer catalysts from unactivated alkyl aziridine and CO2 under mild conditions

Biopolymers made of polysaccharide chains are emerging as promising materials for designing efficient, cheap, environmental friendly and recyclable heterogeneous catalysts. In this study, we synthesized a series of covalently functionalized chitosan-alkyl pyridinium halides (CS-RPX, R = ethyl, propyl, butyl, hexyl and X = Cl, Br) and evaluated their potential application as catalysts for the chemical transformation of CO2 to 4-methyl-2-oxazolidinone using 2-methylaziridine under mild reaction conditions. The catalysts were characterized using different physicochemical methods, including X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), thermo gravimetric analysis (TGA), elemental analysis (EA) and field emission scanning electron microscopy (FE-SEM). 1H NMR, GC-MS, EA and FT-IR were used to confirm successful oxazolidinone formation. Cycloaddition was found to proceed through the synergistic effect of the hydroxyl and amine groups of chitosan together with the anion. The catalyst was reused five times after the cycloaddition reaction, with a loss of 2-6% in conversion and 1-3% in selectivity per cycle. The effect of different reaction parameters, such as catalyst amount, time, temperature and CO2 pressure were studied to determine the reaction conditions that resulted in the highest conversion and selectivity.

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Microwave-assisted preparation of cyclic ureas from diamines in the presence of ZnO

A MW-assisted direct synthesis of cyclic ureas has been developed that proceeds expeditiously in the presence of ZnO thus shortening its reaction time; the process also eliminates the formation of byproducts when compared to the traditional methods involving conventional heating. A microwave-assisted facile method for the preparation of various ureas, cyclic ureas, and urethanes has been developed that affords nearly quantitative yield of products at 120°C (150 W), 71 kPa within 10 min using ZnO as a catalyst. The enhanced selectivity in this reaction is attributed to the deployment of ZnO whose absence results in poor yield and the generation of byproducts.

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.

Aluminium-Catalysed Oxazolidinone Synthesis and their Conversion into Functional Non-Symmetrical Ureas

An efficient and practical aluminium-catalysed approach towards a range of functional oxazolidinones is reported. The method is based on cheap and readily available starting materials including terminal and internal (bicyclic) epoxides and phenyl carbamate. The oxazolidinones serve as highly useful synthons for the high yield preparation of non-symmetrical ureas by nucleophilic ring-opening affording the targeted urea compounds with excellent functional group diversity, high regioselectivity and isolated yields up to >99%.