26654-39-7

Basic information

• Product Name: 4,4-DIMETHYL-2-OXAZOLIDINONE
• Synonyms: 4,4-dimethyl-oxazolidin-2...;4,4-diMethyl-oxazolidin-2-one;ANTI-DMRTA1 (C-TERM) antibody produced in rabbit;DMRTA1;Doublesex- and mab-3-related transcription factor A1;DMO;4,4-DIMETHYL-2-OXAZOLIDINONE;4,4-Dimethyl-1,3-oxazolidin-2-one
• CAS NO: 26654-39-7
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• Mol File: 26654-39-7.mol
• Article Data: 39

Chemical Properties

• Melting Point: 55-56 °C(Solv: ethanol (64-17-5); ligroine (8032-32-4))
• Boiling Point: 272.2 °C at 760 mmHg
• Flash Point: 118.4 °C
• Appearance: /
• Density: 1.039 g/cm³
• Vapor Pressure: 0.00617mmHg at 25°C
• Refractive Index: 1.423
• Storage Temp.: -20°C
• PKA: 12.91±0.40(Predicted)
• CAS DataBase Reference: 4,4-DIMETHYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-DIMETHYL-2-OXAZOLIDINONE(26654-39-7)
• EPA Substance Registry System: 4,4-DIMETHYL-2-OXAZOLIDINONE(26654-39-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 26654-39-7(Hazardous Substances Data)

Usage

General Description

4,4-Dimethyl-2-Oxazolidinone is a chemical compound primarily used as a polar aprotic solvent in organic synthesis and pharmaceutical manufacturing due to its unique capacity to dissolve both polar and non-polar compounds. It is appreciated for its high selectivity, biodegradability, and low toxicity. It exhibits a liquid state at room temperature and is miscible with most organic solvents. This chemical is also used as a spin finish in textile manufacturing. While it is primarily designed for industrial use, precautions must be observed during its handling and storage to prevent exposure and potential health risks.

InChI:InChI=1/C5H9NO2/c1-5(2)3-8-4(7)6-5/h3H2,1-2H3,(H,6,7)

Upstream product

• 854889-97-7 (hydroxy-tert-butyl)-carbamic acid butyl ester 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 105-58-8 Diethyl carbonate 
• 558-30-5 2-methyl-1,2-epoxypropane 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 1659-31-0 2,2'-dipyridyl carbonate 
• 67910-04-7 1-(2-hydroxy-1,1-dimethylethyl)urea 
• 530-62-1 1,1'-carbonyldiimidazole 
• 54013-55-7 4,4-dimethyloxazolidine-2-thione 
• 235780-27-5 cis-1,2-Cyclohexanedimethyl bis[N-(2-hydroxy-1,1-dimethylethyl)carbamate] 
• 7719-09-7 thionyl chloride 
• 543-28-2 isobutylcarbamate 
• 541-41-3 chloroformic acid ethyl ester 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 114341-88-7 3-(2'-bromopropionyl)-4,4-dimethyloxazolidin-2-one 
• 143745-69-1 1-<<4-(1,1-dimethylethyl)-2-methylphenyl>thio>-2-methyl-2-propanamine 
• 2191-60-8 1,1-dimethyl-2-(phenylthio)ethylamine 
• 143745-68-0 1-<(2-methylphenyl)thio>-2-methyl-2-propanamine 
• 60491-95-4 3-bromo-4,4-dimethyl-2-oxazolidinone 
• 176696-08-5 4,6-dimethoxy-7-(4',4'-dimethyl-4',5'-dihydro-oxazol-2'-yl)-2,3-diphenylindole 
• 936140-74-8 3-[4-(2-bromophenyl)-2-phenylbutyryl]-4,4-dimethyloxazolidin-2-one 
• 82760-88-1 3-(2-Bromo-2-phenyl-ethyl)-4,4-dimethyl-oxazolidin-2-one 
• 82760-89-2 3-(2-Hydroxy-2-phenyl-ethyl)-4,4-dimethyl-oxazolidin-2-one 
• 1173175-89-7 3-acetyl-4,4-dimethyloxazolidin-2-one 

Relevant articles and documents

LOW TOXICITY NMP SUBSTITUTES AND USES THEREOF

The present technology is directed to compounds Formulas I, II, III, and IV as well as compositions that include one or more of the compounds and methods of making the compounds. In particular, the present compounds may be used as a replacement for NMP in compositions to produce lower toxicity compositions.

Photocatalytic Intramolecular C-H Amination Using N-Oxyureas as Nitrene Precursors

Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.