2505-98-8

Basic information

• Product Name: 4-Isoxazolecarboxylic acid, 3,5-diphenyl-
• CAS NO: 2505-98-8
• Molecular Formula: C16H11NO3
• Molecular Weight: 265.268
• Mol File: 2505-98-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-Isoxazolecarboxylic acid, 3,5-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isoxazolecarboxylic acid, 3,5-diphenyl-(2505-98-8)
• EPA Substance Registry System: 4-Isoxazolecarboxylic acid, 3,5-diphenyl-(2505-98-8)

Safety Data

• Hazardous Substances Data: 2505-98-8(Hazardous Substances Data)

Upstream product

• 41836-94-6 3-phenyl-4-benzoyl-isoxazol-5-one 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 873-67-6 benzonitrile oxide 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 20615-61-6 bis-phenylpropynoyl peroxide 
• 7299-58-3 phenylpropiolyl chloride 
• 98-88-4 benzoyl chloride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 4850-82-2 ethyl 2-benzoyl-3-oxo-3-phenylpropionate 
• 698-16-8 benzohydroximoyl chloride 
• 1821-34-7 N-chlorobenzamide 
• 63888-21-1 benzyl 3-phenyl-2-propynoate 
• 2289-55-6 methyl [3,5-diphenylisoxazol-4-yl]carboxylate 
• 27046-67-9 bis-(3,5-diphenyl-isoxazole-4-carbonyl) peroxide 

Downstream Products

• 2039-49-8 3,5-diphehylisoxazole 
• 115665-16-2 (3,5-Diphenyl-isoxazol-4-yl)-(4-methoxy-phenyl)-methanone 
• 115665-13-9 (4-Chloro-phenyl)-(3,5-diphenyl-isoxazol-4-yl)-methanone 
• 53646-13-2 3,5-diphenyl-isoxazole-4-carbonyl chloride 
• 108511-94-0 3,5-diphenyl-4-isoxazolylcarbamic acid 1,1-dimethylethyl ester 
• 108512-08-9 N-(3,5-diphenyl-4-isoxazolyl)acetamide 

Relevant articles and documents

Non-Decarboxylative Ruthenium-Catalyzed Rearrangement of 4-Alkylidene-isoxazol-5-ones to Pyrazole- and Isoxazole-4-carboxylic Acids

Treatment of 4-(2-hydroaminoalkylidenyl)- and 4-(2-hydroxyalkylidenyl)-substituted isoxazol-5(4H)-ones with catalytic amounts of [RuCl2(p-cymene)]2, without any additive, afforded pyrazole- and isoxazole-4-carboxylic acids, respectively. The presence of an intramolecular H-bond in these substrates was the key to divert the classical mechanism toward a ring-opening non-decarboxylative path that is expected to generate a vinyl Ru-nitrenoid intermediate, the cyclization of which affords the rearranged products. A gram scale protocol demonstrated the synthetic applicability of this transformation.

Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.

1,3-Dipolar Cycloaddition of Arylnitrile-N-oxides with Methyl 3-Aryl-prop-2-yn-oates and 1-Aryl-3-phenyl-prop-2-yn-1-ones

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