19836-78-3

Basic information

• Product Name: 3-METHYL-2-OXAZOLIDONE
• Synonyms: 3-methyl-2-oxazolidinon;3-methyl-oxazolidin-2-one;3-methyloxazolidine-2-one;N-Methyl-2-oxazolidinone;N-Methyl-2-oxazolidone;N-Methyloxazolidone;3-METHYL-2-OXAZOLIDINONE;3-METHYL-2-OXAZOLIDONE
• CAS NO: 19836-78-3
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• EINECS: 243-361-1
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Oxazolines/Oxazolidines
• Mol File: 19836-78-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 15 °C(lit.)
• Boiling Point: 87-90 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.17 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00877mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• PKA: -1.34±0.20(Predicted)
• CAS DataBase Reference: 3-METHYL-2-OXAZOLIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-2-OXAZOLIDONE(19836-78-3)
• EPA Substance Registry System: 3-METHYL-2-OXAZOLIDONE(19836-78-3)

Safety Data

• WGK Germany: 3
• RTECS: RQ3550000
• Hazardous Substances Data: 19836-78-3(Hazardous Substances Data)

Usage

Uses

3-Methyl-2-oxazolidinone mixed with ethylene carbonate or dimethyl carbonate in the presence of lithium tetrafluoroborate or lithium hexafluorophosphate has been used as an electrolyte in lithium batteries.

Purification Methods

Purify the oxazolidone by successive fractional freezing, then dry it in a dry-box over 4A molecular sieves for 2 days. Distil it under high vacuum and store it dry as before. [Beilstein 27 III/IV 2517.]

InChI:InChI=1/C4H7NO2/c1-5-2-3-7-4(5)6/h2-3H2,1H3

Upstream product

• 22074-92-6 methyl-carbamic acid-(2-chloro-ethyl ester) 
• 497-25-6 dimethylenecyclourethane 
• 74-83-9 methyl bromide 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 5852-49-3 5-phenyl-1,3,4-oxathiazol-2-one 
• 124-38-9 carbon dioxide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 107-06-2 1,2-dichloro-ethane 
• 74-89-5 methylamine 
• 1125651-04-8 C₇₀H₆₇N₅O₁₅ 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 616-38-6 carbonic acid dimethyl ester 
• 105-58-8 Diethyl carbonate 
• 145459-16-1 N-methyl-N-(2-nitrooxyethyl)ammonium nitrate 

Downstream Products

• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 34557-54-5 methane 
• 27970-32-7 3-methyl-1,3-oxazolidine 
• 1261063-42-6 3-methyl-4-(2,4,6-trimethoxyphenyl)-1,3-oxazolidin-2-one 
• 1261063-53-9 3-[(2,4,6-trimethoxyphenyl)methyl]-1,3-oxazolidin-2-one 
• 1250801-81-0 C₁₁H₁₈N₂O 
• 116089-55-5 N,N’-dimethyl-N-(o-tolyl)ethane-1,2-diamine 
• 2412-49-9 N,N'-dimethyl-N-phenyl-1,2-ethanediamine 
• 55080-47-2 N-ethyl-N'-methyl-N-phenyl-ethylenediamine 
• 74418-14-7 C₁₁H₁₅F₃N₂ 
• 1340503-86-7 C₁₀H₁₅ClN₂ 
• 1248916-13-3 C₁₀H₁₅FN₂ 
• 1247199-90-1 C₁₁H₁₈N₂ 
• 66711-48-6 N-benzyl-N'-methyl-N-phenylethylenediamine 

Relevant articles and documents

Design, synthesis and antimalarial evaluation of novel thiazole derivatives

As part of our medicinal chemistry program's ongoing search for compounds with antimalarial activity, we prepared a series of thiazole analogs and conducted a SAR study analyzing their in vitro activities against the chloroquine-sensitive Plasmodium falciparum 3D7 strain. The results indicate that modifications of the N-aryl amide group linked to the thiazole ring are the most significant in terms of in vitro antimalarial activity, leading to compounds with high antimalarial potency and low cytotoxicity in HepG2 cell lines. Furthermore, the observed SAR implies that non-bulky, electron-withdrawing groups are preferred at ortho position on the phenyl ring, whereas small atoms such as H or F are preferred at para position. Finally, replacement of the phenyl ring by a pyridine affords a compound with similar potency, but with potentially better physicochemical properties which could constitute a new line of research for further studies.

Self-immolative polymers containing rapidly cyclizing spacers: Toward rapid depolymerization rates

Self-immolative polymers containing 4-hydroxybenzyl alcohol alternating with either N-methylaminoethanol or 2-mercaptoethanol spacers were synthesized and demonstrated to controllably depolymerize in response to the cleavage of a stabilizing end-cap from

5-Aryl-2-oxo-1,2,4-oxathiazoles as Cyclocarbonylating Agents for 2-Aminoalcohols and 1,2-Diamines

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Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene

The first example for the photocatalytic generation of a highly electrophilic intermediate that is not based on radical reactivity is reported. The single-electron reduction of bench-stable and commercially available 4-(trifluoromethoxy)benzonitrile by an organic photosensitizer leads to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge-transfer complex-dimer as the catalytic active species. Fluorophosgene as a highly reactive intermediate, was indirectly detected via its next downstream carbonyl fluoride intermediate by NMR. Furthermore, detailed NMR analyses provided a comprehensive reaction mechanism including a water dependent off-cycle equilibrium.

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.