491875-99-1

Basic information

• Product Name: Isoxazole, 3-(4-fluorophenyl)-5-methyl-
• Synonyms: LHFLXLRCDZEKPV-UHFFFAOYSA
• CAS NO: 491875-99-1
• Molecular Formula: C10H8FNO
• Molecular Weight: 177.17500
• Mol File: 491875-99-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 48-50 °C
• Boiling Point: 279.8±25.0 °C(Predicted)
• Density: 1.171±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Isoxazole, 3-(4-fluorophenyl)-5-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 3-(4-fluorophenyl)-5-methyl-(491875-99-1)
• EPA Substance Registry System: Isoxazole, 3-(4-fluorophenyl)-5-methyl-(491875-99-1)

Safety Data

• Hazardous Substances Data: 491875-99-1(Hazardous Substances Data)

Upstream product

• 49750-46-1 p-fluorobenzonitrile oxide 
• 106-96-7 propargyl bromide 
• 904672-47-5 1-(4-fluorophenyl)but-3-en-1-one oxime 
• 86718-78-7 1-(4-fluorophenyl)-3-buten-1-ol 
• 459-57-4 4-fluorobenzaldehyde 
• 1736-21-6 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 459-23-4 4-fluorobenzaldoxime 
• 42202-95-9 4-fluoro-N-hydroxybenzimidoyl chloride 
• 833462-37-6 3-(4-fluorophenyl)-5-[(phenylselanyl)methyl]-4,5-dihydroisoxazole 
• 393165-20-3 (Z)-N-hydroxy-4-fluoro-benzenecarboximidoyl chloride 
• 867203-96-1 3-(4-fluorophenyl)-5-iodomethylisoxazoline 
• 61668-02-8 1-(4-fluorophenyl)but-3-en-1-one 
• 329-79-3 1-(4-fluorophenyl)ethanone oxime 

Downstream Products

• 491876-00-7 4-bromo-3-(4-fluorophenyl)-5-methyl-isoxazole 
• 491876-02-9 C₁₀H₉BFNO₃ 

Relevant articles and documents

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Reaction of allenylmagnesium and allenylindium bromides with nitrile oxides: synthesis of novel 5-butynyl- and 5-methylisoxazoles

5-Butynylisoxazoles were obtained in high yields through a domino addition, C-O heterocyclization involving allenylmagnesium bromide and benzonitrile oxide in dry THF, in which the corresponding 5-methylisoxazoles were isolated in trace amounts. However, when the reactions were attempted in aqueous media using allenylindium bromide, 5-methylisoxazoles were formed as the sole products in high yields.

Convenient Approach to 3,4-Diarylisoxazoles Based on the Suzuki Cross-Coupling Reaction

The Suzuki cross-coupling reaction was found effective for rapid access to a series of 3,4-diarylisoxazoles of pharmacological interest. The efficiency of this approach was demonstrated by the synthesis of the highly potent COX-2-selective inhibitor, 4-(5-methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide (valdecoxib), and its analogues. Thus, the coupling reaction between (3-aryl-5-methyl-4-isoxazolyl)boronic acids, prepared in situ from the corresponding bromides using triisopropyl borate, and aryl bromides containing a 4-sulfonamide or 4-methylsulfonyl group under the standard conditions [Pd(PPh3)4, Na2CO3, EtOH-H2O, reflux] yielded the target 3,4-diarylisoxazoles in good yields.