939-05-9

Usage

Uses

Used in Pharmaceutical Industry:
3(2H)-Isoxazolone,5-phenyl-(9CI) is used as a pharmaceutical agent for its anti-inflammatory and analgesic properties. It can potentially be developed into drugs for treating various inflammatory and pain-related conditions, offering an alternative to existing medications.
Used in Agrochemical Industry:
3(2H)-Isoxazolone,5-phenyl-(9CI) is used as an agrochemical agent, leveraging its biological activities to control or manage pests and diseases in agriculture. Its potential applications may include the development of novel pesticides or herbicides that can effectively protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
3(2H)-Isoxazolone,5-phenyl-(9CI) is used as a synthetic intermediate in the preparation of various organic compounds and materials. Its unique structure and reactivity make it a valuable building block for the synthesis of complex molecules, which can find applications in different industries, such as pharmaceuticals, materials science, and specialty chemicals.

InChI:InChI=1/C9H7NO2/c11-9-6-8(12-10-9)7-4-2-1-3-5-7/h1-6H,(H,10,11)

Upstream product

• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 85127-44-2 ethyl 3-phenyl-3-(p-tolylamino)acrylate 
• 53256-22-7 ethyl β-anilinocinnamate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 85127-43-1 ethyl β-(p-nitroanilino)cinnamate 
• 85127-45-3 methyl 3-(2H-imidazol-1-yl)-3-phenylacrylate 
• 127-07-1 N-hydroxyurea 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 260782-36-3 N-(tert-butoxycarbonyl)-N-(tert-butoxycarbonyloxy)benzoylacetamide 
• 82961-73-7 5-((hydroxy)(phenyl)methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 129235-28-5 3-methanesulfonyloxy-5-phenyl-isoxazole 
• 81282-03-3 5-phenyl-3-(p-toluenesulphonyloxy)isoxazole 
• 958668-81-0 3-[(4-chlorobut-2-yn-1-yl)oxy]-5-phenylisoxazole 
• 195715-24-3 3-(2-bromoethoxy)-5-phenylisoxazole 
• 119116-10-8 5-phenyl-2-(2-nitro-4-trifluoromethylphenyl)-4-isoxazolin-3-one 
• 126312-02-5 3-(2,3-epoxypropoxy)-5-phenylisoxazole 
• 26347-24-0 3-benzyloxy-5-phenyl-isoxazole 
• 115371-89-6 diethyl 2-(5-methyl-3-isoxazolyloxy)malonate 
• 195714-54-6 3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazole 
• 183284-33-5 3-Methoxymethoxy-5-phenylisoxazole 
• 69700-37-4 2-allyl-3-chloro-5-phenyl-isoxazolium; chloride 
• 68471-17-0 3-chloro-2-isopropyl-5-phenyl-isoxazolium; chloride 
• 69528-59-2 2-allyl-5-phenyl-isoxazole-3-thione 
• 70000-80-5 2-isopropyl-5-phenyl-isoxazole-3-thione 

Relevant academic research and scientific papers

A novel route to 5-substituted 3-isoxazolols. Cyclization of N,O-diBoc β-keto hydroxamic acids synthesized via acyl Meldrum's acids

3-Isoxazolols are most often synthesized from a β-keto ester and hydroxylamine. This cyclization typically gives rise to a major byproduct, the corresponding 5-isoxazolone. We have found that N,O-diBoc-protected β- keto hydroxamic acids can be synthesized and cyclized to 5-substituted 3- isoxazolols without formation of any byproduct. We present a novel and versatile three-step procedure in which carboxylic acid derivatives are converted into acyl Meldrum's acids which, upon aminolysis with N,O-bis(tert- butoxycarbonyl)hydroxylamine, lead to the N,O-diBoc-protected β-keto hydroxamic acids. These hydroxamic acid analogues were then, upon treatment with hydrochloric acid, cyclized to the corresponding 5-substituted 3- isoxazolols.

(Phenylalkylaminoalkyloxy)-heteroaryl-compounds, processes and intermediates for their production and pharmaceutical compositions containing them

3-(Phenylalkylaminoalkylozy)-heteroaryl compounds having heart rate lowering and/or anti-ischemic effects, methods for their preparation and pharmaceutical compositions containing them are described. The compounds correspond to the general formula I STR1 or to the general formula XXXI STR2 in which the substituents have the meanings given the specification.

Synthesis of 3-Hydroxyisoxazoles from β-Ketoesters and Hydroxylamine

An efficient synthesis of 3-hydroxyisoxazoles from β-ketoesters and hydroxylamine was investigated.The reaction of the sodium salts of β-ketoesters and hydroxylamine at a low temperature, followed by quenching with an excess of conc.HCl under heating gave predominantly 3-hydroxyisoxazoles involving 4-sulfenylated 3-hydroxyisoxazoles.Starting from the prepared 4-(2,4-dichlorobenzyl)-3-hydroxy-5-methylisoxazole, a potential herbicidal compound, 4-(2,4-dichlorobenzoyl)-3-hydroxy-5-methylisoxazole, was also synthesized in five steps.

Action de l'hydroxyuree sur les esters α-acetyleniques

Hydroxyurea, in its oxanion form NH2-CO-NHO(1-), reacts in basic medium by a 1,4-addition to α-acetylenic esters leading to the E and Z ethylenic β-ureidoxy esters isomers.The E isomer can be isolated and identified from reaction with ethyl tetrolate and ethyl propiolate.The Z isomer undergoes cyclisation in situ to give the 2-carboxamido-5-methyl-3-isoxazolone.With phenyl propiolate, the 3-hydroxy-5-phenyl isoxazole is directly obtained without isolation of the intermediate N-carboxamido derivative.In the case of ethyl propiolate two cyclic compounds are obtained: 3-hydroxyisoxazole and 2-N-carboxamido-5-ethoxy-3-isoxazolidinone.The formation of the former is due to the in situ cyclisation of the Z isomer.The isolation of the latter compound can be explained by solvent addition to the E β-ureidoxyacrylate intermadiate in a Michael addition followed by cyclisation.