24474-93-9

Basic information

• Product Name: 2-methyl-5(4H)-oxazolone
• Synonyms: 2-methyl-5(4H)-oxazolone;5(4H)-Oxazolone, 2-Methyl-
• CAS NO: 24474-93-9
• Molecular Formula: C₄H₅NO₂
• Molecular Weight: 99.09
• Mol File: 24474-93-9.mol

Chemical Properties

• Boiling Point: 119.1°C at 760 mmHg
• Flash Point: 39.3°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 16.2mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 2-methyl-5(4H)-oxazolone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-5(4H)-oxazolone(24474-93-9)
• EPA Substance Registry System: 2-methyl-5(4H)-oxazolone(24474-93-9)

Safety Data

• Hazardous Substances Data: 24474-93-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
2-Methyl-5(4H)-oxazolone is used as a chemical intermediate for the synthesis of various complex organic molecules and pharmaceutical compounds. Its unique structure allows for versatile chemical reactions and modifications, making it a valuable building block in organic chemistry.
Used in Multireference Configuration Interaction Studies:
In the field of computational chemistry, 2-methyl-5(4H)-oxazolone is employed as a subject for multireference configuration interaction studies with singles and doubles of some mesoionic rings. These studies aim to determine reaction and activation free energies for the ring-opening reaction, providing valuable insights into the reaction mechanisms and potential applications of this compound.
Used in Pharmaceutical Development:
Due to its unique chemical properties, 2-methyl-5(4H)-oxazolone has potential applications in the development of new pharmaceuticals. Its ability to form various derivatives and interact with different biological targets makes it a promising candidate for the design of novel drugs with specific therapeutic effects.
Used in Material Science:
The unique structure and properties of 2-methyl-5(4H)-oxazolone also make it a candidate for the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. Its potential applications in material science could lead to the creation of advanced materials for various industries, including electronics, energy, and environmental protection.

Synthesis Reference(s)

Synthesis, p. 418, 1984 DOI: 10.1055/s-1984-30859

InChI:InChI=1/C4H5NO2/c1-3-5-2-4(6)7-3/h2H2,1H3

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 543-24-8 N-acetylglycine 
• 108-24-7 acetic anhydride 
• 56-40-6 glycine 

Downstream Products

• 38879-46-8 (Z)-4-benzylidene-2-methyl-5(4H)-oxazolone 
• 77008-44-7 α-acetamidocinnamanilide 
• 66949-13-1 (Z)-2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one 
• 55636-13-0 2-acetylaminocinnamanilide 
• 779-30-6 3-acetamidocoumarin 
• 155626-70-3 2-methyl-4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene-4,5-dihydro-oxazol-5-one 
• 7606-79-3 N-acetyl-glycine-N'-methylamide 
• 52507-17-2 (Z)-4-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)phenyl acetate 
• 60470-82-8 (Z)-2-methoxy-4-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)phenyl acetate 
• 38879-47-9 (Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone 
• 93634-55-0 (Z)-4-(4-chlorobenzylidene)-2-methyloxazol-5(4H)-one 
• 71198-72-6 (4Z)-4-(4-methoxybenzylidene)-2-methyl-oxazolin-5-one 
• 33404-13-6 3-acetamido-6-bromo-2H-chromen-2-one 
• 3969-09-3 2-methyl-5-phenyl-1,3-oxazole 

Relevant articles and documents

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An efficient two-step synthetic procedure for the preparation of numerous variations of N-protected α,β-unsaturated α-amino acids and their corresponding esters from N-protected glycine and either aliphatic or aromatic aldehydes was developed. The reaction involved cyclization of the N-protected glycine into oxazolone, condensation with the aldehyde, and ring opening with a base. Copyright Taylor & Francis Group, LLC.

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A kinetic study of the base-catalyzed dimerization of 5(4H)-oxazolones

The effects of the substituent at position-2 and kind of the base on the rate of the base-catalyzed dimerization of 5(4H)-oxazolones have been investigated. The electrondonating and strong steric effect of the substituent at position-2 reduce markedly the proclivity of 5(4H)-oxazolones to dimerization. The following catalytic activity sequence of the bases has been found: DBU >> Et3N > (i-Pr)2EtN.

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