2546-21-6

Basic information

• Product Name: 3-(4-fluorophenyl)-5-methyl-N-phenylisoxazole-4-carboxamide
• Synonyms: 3-(4-fluorophenyl)-5-methyl-N-phenylisoxazole-4-carboxamide
• CAS NO: 2546-21-6
• Molecular Weight: 296.301
• Mol File: 2546-21-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-(4-fluorophenyl)-5-methyl-N-phenylisoxazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorophenyl)-5-methyl-N-phenylisoxazole-4-carboxamide(2546-21-6)
• EPA Substance Registry System: 3-(4-fluorophenyl)-5-methyl-N-phenylisoxazole-4-carboxamide(2546-21-6)

Safety Data

• Hazardous Substances Data: 2546-21-6(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 1736-21-6 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 459-23-4 4-fluorobenzaldoxime 
• 459-57-4 4-fluorobenzaldehyde 
• 42202-95-9 4-fluoro-N-hydroxybenzimidoyl chloride 
• 102-01-2 N-phenylacetoacetamide 

Relevant articles and documents

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

Herein we report a method for the synthesis of 3,4,5-trisubstituted isoxazoles in water under mild basic conditions at room temperature via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides. We optimized the reaction conditions to control the selectivity of the production of isoxazoles and circumvent other competing reactions, such as O-imidoylation or hetero [3 + 2]-cycloaddition. The reaction happens fast in water and completes within 1-2 hours, which provides an environmentally friendly access to 3,4,5-trisubstituted isoxazoles, an important class of structures found in numerous bioactive natural products and pharmaceuticals. Additionally, we optimized the reaction conditions to produce trifluoromethyl-substituted isoxazoles, a prevalent scaffold in biomedical research and drug discovery programs. We also proposed a plausible mechanism for the selectivity of the [3 + 2]-cycloaddition reaction to produce 3,4,5-trisubstituted isoxazoles. Not to be overlooked are our optimized reaction conditions for the dimerization of hydroximoyl chlorides to form furoxans also known as 1,2,5-oxadiazole 2-oxides, a class of structures with important biological activities due to their unique electronic nature and coordination ability.

Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: Direct access to 3,4,5-trisubstituted isoxazoles

TMG-catalyzed [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of β-functionalized ketones with nitrile oxides have been developed. This strategy could generate 3,4,5-trisubstituted isoxazoles in high yields and regioselectivities.