939-05-9

Basic information

• Product Name: 3(2H)-Isoxazolone,5-phenyl-(9CI)
• Synonyms: 3(2H)-Isoxazolone,5-phenyl-(9CI);3-Hydroxy-5-phenylisoxazole;3-Hydroxy-5-phenylisoxazole(α-form);5-Phenyl-3-hydroxyisoxazole;5-phenyl-3-Isoxazolol;5-phenyl-4-Isoxazolin-3-one;β-3-Hydroxy-5-phenylisoxazole;5-phenyl-1,2-oxazol-3-one
• CAS NO: 939-05-9
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• Product Categories: OXAZOLE
• Mol File: 939-05-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 163-164 °C
• Boiling Point: 372.7°Cat760mmHg
• Flash Point: 179.2°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 4.39E-06mmHg at 25°C
• Refractive Index: 1.587
• PKA: 12.07±0.40(Predicted)
• CAS DataBase Reference: 3(2H)-Isoxazolone,5-phenyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3(2H)-Isoxazolone,5-phenyl-(9CI)(939-05-9)
• EPA Substance Registry System: 3(2H)-Isoxazolone,5-phenyl-(9CI)(939-05-9)

Safety Data

• Hazardous Substances Data: 939-05-9(Hazardous Substances Data)

Usage

General Description

3(2H)-Isoxazolone,5-phenyl-(9CI) is a chemical compound with the molecular formula C9H7NO2. 3(2H)-Isoxazolone,5-phenyl-(9CI) belongs to the isoxazolone class of organic compounds and contains a five-membered ring with an oxygen and nitrogen atom. It is also characterized by a phenyl group attached to the ring structure. This chemical has potential applications in pharmaceuticals and agrochemicals due to its diverse biological activities, including anti-inflammatory and analgesic properties. Additionally, it may also have uses in the synthesis of various organic compounds and materials due to its unique structure and reactivity.

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

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

Downstream Products

• 24506-17-0 3-hydroxy-3-phenylpropionamide 
• 81282-03-3 5-phenyl-3-(p-toluenesulphonyloxy)isoxazole 
• 26347-24-0 3-benzyloxy-5-phenyl-isoxazole 
• 115371-89-6 diethyl 2-(5-methyl-3-isoxazolyloxy)malonate 
• 126312-02-5 3-(2,3-epoxypropoxy)-5-phenylisoxazole 
• 119116-10-8 5-phenyl-2-(2-nitro-4-trifluoromethylphenyl)-4-isoxazolin-3-one 
• 195714-54-6 3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazole 
• 183284-33-5 3-Methoxymethoxy-5-phenylisoxazole 
• 195715-24-3 3-(2-bromoethoxy)-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 
• 76422-48-5 4,5-diphenyl-3-(p-toluenesulphonyloxy)isoxazole 

Relevant articles and documents

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.

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.

Regioselective synthesis of 3-hydroxyisoxazoles and 5-isoxazolones from β-amino α,β-unsaturated esters

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