708-57-6

Basic information

• Product Name: 5-methyl-3-phenyl-1,3-oxazolidin-2-one
• Synonyms: 5-methyl-3-phenyl-1,3-oxazolidin-2-one
• CAS NO: 708-57-6
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.19984
• Mol File: 708-57-6.mol
• Article Data: 35

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-methyl-3-phenyl-1,3-oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-3-phenyl-1,3-oxazolidin-2-one(708-57-6)
• EPA Substance Registry System: 5-methyl-3-phenyl-1,3-oxazolidin-2-one(708-57-6)

Safety Data

• Hazardous Substances Data: 708-57-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2177, 1986 DOI: 10.1021/jo00362a005

Upstream product

• 103-71-9 phenyl isocyanate 
• 75-56-9 methyloxirane 
• 108-32-7 1,2-propylene cyclic carbonate 
• 62-53-3 aniline 
• 103-72-0 phenyl isothiocyanate 
• 127213-88-1 [4-Methyl-[1,3]dioxolan-(2E)-ylidene]-phenyl-amine 
• 102879-24-3 2-methyl-N-phenylaziridine 
• 124-38-9 carbon dioxide 
• 101-99-5 N-carboethoxyaniline 
• 102-09-0 bis(phenyl) carbonate 
• 3233-06-5 1-anilino-propan-2-ol 
• 26198-63-0 1,2-Dichloropropane 
• 345305-22-8 (2S)-1-N-Phenylamino-2-propanol 
• 616-38-6 carbonic acid dimethyl ester 

Relevant articles and documents

Synergetic activation of CO2by the DBU-organocatalyst and amine substrates towards stable carbamate salts for synthesis of oxazolidinones

The development of an efficient methodology to transform CO2 into valuable chemicals has attracted increasing attention concerning the challenging issues of CO2-utilization. Herein, an efficient approach for the preparation of oxazolidinones from CO2, primary (aliphatic/aromatic) amines and 1,2-dichloroethane (or its derivatives) catalyzed by DBU organo-superbase was achieved with yields of 47-97% under mild conditions (80-100 °C, 12 h, 1.0 MPa CO2). Control experiments demonstrated that the formation of an ion-pair carbamate salt intermediate IS-B derived from the reaction of CO2, DBU (catalyst) and an amine (substrate) was the key step for this three-component reaction. The available DBU-amine-CO2 adduct intermediate (like IS-B-2) with fair stability will evolve into the thermodynamically stable product oxazolidinones upon attack of 1,2-dichloroethane (or its derivatives), along with the regeneration of the DBU catalyst. Alternatively, the decomposition of the DBU-aryl amine-CO2 adduct (like IS-B-1) with relatively poor stability also could result in the competitive substitution reaction of 1,2-dichloroethane (or its derivatives) with the aryl amine. This work provides insights into synergetic CO2-activation by the DBU-catalyst and a nucleophilic amine-substrate via the formation of robust carbamate salt intermediates responsible for the final production of oxazolidinones. This journal is

Catalytic Dealkylative Synthesis of Cyclic Carbamates and Ureas via Hydrogen Atom Transfer and Radical-Polar Crossover

Guided by the transition-metal hydrogen atom transfer and radical-polar crossover concepts, we developed a functional-group-tolerant and scalable method for the synthesis of cyclic carbamates and ureas, which are found in the structures of bioactive compo

A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare-Earth Metal Amides

Three-component reaction of epoxides, amines, and dimethyl carbonate catalyzed by rare-earth metal amides has been developed to synthesize oxazolidinones. 47 examples of 3,5-disubstituted oxazolidinones were prepared in 13–97 % yields. This is a simple and most practical method which employs easily available substrates and catalysts, and is applicable to a wide range of aromatic and aliphatic amines, as well as mono-substituted epoxides. Scope of disubstituted epoxides is rather limited, which requires further study. Preliminary mechanistic study reveals two possible reaction pathways through intermediates of β-amino alcohols or amides.