61428-21-5

Basic information

• Product Name: Isoxazole, 3-(4-methoxyphenyl)-5-methyl-
• CAS NO: 61428-21-5
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Mol File: 61428-21-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Isoxazole, 3-(4-methoxyphenyl)-5-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 3-(4-methoxyphenyl)-5-methyl-(61428-21-5)
• EPA Substance Registry System: Isoxazole, 3-(4-methoxyphenyl)-5-methyl-(61428-21-5)

Safety Data

• Hazardous Substances Data: 61428-21-5(Hazardous Substances Data)

Upstream product

• 5874-09-9 methyl (4-methoxyphenyl)carbodithioate 
• 74903-79-0 N-hydroxy-4-methoxybenzenecarboximidoyl chloride 
• 106-96-7 propargyl bromide 
• 15500-73-9 4-methoxybenzonitrile oxide 
• 102252-89-1 (Z)-3-amino-1-(4-methoxyphenyl)but-2-en-1-one 
• 4749-28-4 2-nitropropene 
• 85234-21-5 1-(4-methoxyphenyl)but-3-en-1-one 
• 24165-60-4 1-(4-methoxyphenyl)but-3-en-1-ol 
• 904672-46-4 1-(4-methoxyphenyl)but-3-en-1-one oxime 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 828939-56-6 3-(4-methoxyphenyl)-5-[(phenylselanyl)methyl]-4,5-dihydroisoxazole 
• 206055-86-9 3-(4-methoxyphenyl)-5-(hydroxymethyl)isoxazole 
• 123-11-5 4-methoxy-benzaldehyde 
• 338982-43-7 1-(3-(4-methoxyphenyl)isoxazol-5-yl)methaneamine 

Relevant articles and documents

Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N-O Bond Formation

An efficient new synthesis of 3,5-bis(het)arylisoxazoles, involving the reaction of 1,3-bis(het)arylmonothio-1,3-diketones with sodium azide in the presence of IBX catalyst, has been reported. The reaction proceeds at room temperature in high yields and is applicable to a broad range of substrates including the synthesis of 5-methyl-3-arylisoxazoles, a key subunit present in several β-lactamase-resistant antibiotics. A probable mechanism for the formation of isoxazoles has been suggested. A few of the 5-styryl/arylbutadienyl-3-(het)arylisoxazoles have also been synthesized by reacting the corresponding 1-(het)aryl-1-(methylthio)-4-(het)arylidene-but-1-en-3-ones with sodium azide at higher temperatures. The reaction of β-ketodithioesters with sodium azide is shown to furnish β-ketonitriles in good yields.

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).

Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity

Efficient routes for the regioselective synthesis of 3,5-bis(het)arylisoxazoles with complementary regioselectivity have been developed. The methods involve the cyclocondensation of hydroxylamine hydrochloride with either 1,3-bis(het)aryl-monothio-substituted 1,3-diketones 1 or with 3-methylthio-1,3-bis(het)aryl-2-propenones 2 under various reaction conditions. In the first protocol, diketones 1 were treated with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene to give 3,5-bis(het)arylisoxazoles 5, in which the het(aryl) moiety attached to thiocarbonyl group of the monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het)arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors 1 and 2 has been suggested.