3672-52-4

Basic information

• Product Name: 5-Phenyl-3-(4-methoxyphenyl)isoxazole
• Synonyms: 3-(4-Methoxyphenyl)-5-phenylisoxazole;5-Phenyl-3-(4-methoxyphenyl)isoxazole
• CAS NO: 3672-52-4
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.2799
• Mol File: 3672-52-4.mol

Chemical Properties

• Boiling Point: 429.3°Cat760mmHg
• Flash Point: 213.4°C
• Appearance: /
• Density: 1.142g/cm³
• Vapor Pressure: 3.55E-07mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: 5-Phenyl-3-(4-methoxyphenyl)isoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Phenyl-3-(4-methoxyphenyl)isoxazole(3672-52-4)
• EPA Substance Registry System: 5-Phenyl-3-(4-methoxyphenyl)isoxazole(3672-52-4)

Safety Data

• Hazardous Substances Data: 3672-52-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H13NO2/c1-18-14-9-7-12(8-10-14)15-11-16(19-17-15)13-5-3-2-4-6-13/h2-11H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 6327-79-3 1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione 
• 2475-92-5 4-methoxyacetophenone oxime 
• 67-56-1 methanol 
• 64-19-7 acetic acid 
• 1004-22-4 (phenylethynyl)sodium 
• 38435-51-7 N-hydroxy-4-methoxy-benzenecarboximidoyl chloride 
• 17064-22-1 2-(4-methoxyphenyl)-5-phenyl oxazole 
• 146933-25-7 3-(4-methoxyphenyl)-5-phenyl-4,5-dihydroisoxazol-5-ol 
• 536-74-3 phenylacetylene 
• 5468-44-0 α-nitrostyrene 
• 15500-73-9 4-methoxybenzonitrile oxide 
• 7664-93-9 sulfuric acid 

Downstream Products

• 80223-00-3 3-(4-Methoxy-phenyl)-2-methyl-5-phenyl-isoxazol-2-ium; iodide 
• 22439-72-1 3-(4-hydroxyphenyl)-5-phenylisoxazole 
• 70312-74-2 1-(2,2-diphenyl-ethenesulfonyl)-4-methyl-benzene 

Relevant articles and documents

Green preparation method of isoxazole compound participating in water-soluble vitamin E

The invention provides a green synthesis method of an isoxazole compound represented by the formula (III), wherein the aldehyde oxime compound represented by the formula (I) is a substrate and is in an aqueous solution of a surfactant with a mass concentration 1 wt % - 5 wt % in N - chlorosuccinimide. The alkyne compound represented by the formula (II) is reacted 6 - 16h at room temperature under the common action of the basic substance, and the resulting reaction solution is post-treated to obtain the isoxazole compound represented by the formula (III). Water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized.

3, 5-disubstituted isoxazole derivative and synthesis method thereof

The invention provides a 3, 5-disubstituted isoxazole derivative and a synthesis method thereof, and belongs to the technical field of organic synthesis medicines and medical intermediates. The method comprises the following steps: adding a proper solvent

TEMPO-Mediated Selective Synthesis of Isoxazolines, 5-Hydroxy-2-isoxazolines, and Isoxazoles via Aliphatic δ-C(sp3)-H Bond Oxidation of Oximes

Selective synthesis of three different bioactive heterocycles; isoxazolines, 5-hydroxy-2-isoxazolines and isoxazoles from the same starting material using TEMPO (2,2,6,6-Tetramethylpiperidin-1-oxyl) as a radical initiator is reported. Selectivity was achi

Complementary and Regioselective Synthesis of Isomeric 3-[Isoxazol-3(or 5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones

A simple and efficient method for the complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles has been developed by the regioselective cyclocondensation reaction of β-ethylthio-β-indolyl-α,β-unsaturated ketones and hydroxylamine hydrochloride. It was found that the cyclocondensation reaction in the presence of excess NaOEt in refluxing EtOH gives 3-(isoxazol-5-yl)indoles in good yields, whereas using NaOAc in boiling AcOH gives 3-(isoxazol-3-yl)indoles in good yields.

Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate

An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.

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.

Catalyst control in positional-selective C-H alkenylation of isoxazoles and a ruthenium-mediated assembly of trisubstituted pyrroles

High levels of catalyst control are demonstrated in determining the positional selectivity in C-H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C(sp2)-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C(sp2)-H activation at the distal position of the directing group. Synthetic elaboration of this C-H alkenylation product via ruthenium and copper co-catalysis leads to an efficient method for the assembly of densely substituted pyrroles.

A convenient one-pot synthesis of 3,5-diarylisoxazoles via oxidative cyclisation using catalytic CuBr2 and oxone

A facile one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones and hydroxylamine hydrochloride is reported. The reaction is efficiently promoted by catalytic CuBr2 and Oxone to afford the desired products mostly in high yields

Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes

A rhodium-catalyzed cascade annulative coupling of 3,5-diarylisoxazoles with three equivalents of an alkyne proceeds smoothly in the presence of a Cu(II) oxidant, where the sequential construction of isoquinoline and naphtho[1,8- bc ]pyran frameworks connected by a biaryl linkage is achieved by a single operation. Most of the obtained polycyclic compounds exhibit visible fluorescence in both the solution and the solid state. The hexaphenylated isoquinoline-naphthopyran conjugate (R = Ph) as a representative product shows a green emission which can be turned off by making an isoquinolinium salt with an acid. The emission is also reversibly turned on by treatment with a base.

An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.