1199-00-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-5-phenyl-1,2,4-oxadiazole is used as a key intermediate in the synthesis of various pharmaceuticals for its potential biological activities. Its anti-inflammatory, antioxidant, and antitumor properties make it a valuable component in the development of new drugs targeting a range of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Methyl-5-phenyl-1,2,4-oxadiazole serves as a building block in the creation of agrochemicals. Its incorporation into these products can enhance their effectiveness in protecting crops and improving agricultural yields.
Used in Materials Science:
3-Methyl-5-phenyl-1,2,4-oxadiazole is utilized in the development of advanced materials due to its unique chemical properties. It contributes to the improvement of material characteristics such as stability, reactivity, and other desirable traits in various applications.
Used in Organic Electronics:
As a component in organic electronic materials, 3-Methyl-5-phenyl-1,2,4-oxadiazole plays a role in enhancing the performance of devices such as organic light-emitting diodes (OLEDs) and organic solar cells, thanks to its electronic properties.
Used as a Fluorescence Probe in Biomedical Applications:
3-Methyl-5-phenyl-1,2,4-oxadiazole is employed as a fluorescence probe in biomedical research. Its optical properties allow for its use in imaging and sensing applications, contributing to advancements in the study and diagnosis of diseases.

InChI:InChI=1/C9H8N2O/c1-7-10-9(12-11-7)8-5-3-2-4-6-8/h2-6H,1H3

Upstream product

• 87277-54-1 ethyl N-benzoylacetimidate 
• 98-88-4 benzoyl chloride 
• 118493-85-9 acetamide oxime 
• 35787-71-4 thianthrene cation radical perchlorate 
• 932-90-1 Benzaldoxime 
• 953819-82-4 C₁₃H₁₆N₂O₂ 
• 100-47-0 benzonitrile 
• 62539-46-2 2,4,4-trimethyloxazoline 2,3-oxide 
• 124-42-5 acetamidine hydrochloride 
• 108-88-3 toluene 
• 5692-19-3 N-benzoylacetamidine 
• 65-85-0 benzoic acid 
• 4937-86-4 1-phenyl-1,2-propanedione dioxime 
• 87277-54-1 N-Benzoylacetimidsaeure-ethylester 

Downstream Products

• 27350-74-9 5-butyl-3-methyl-5-phenyl-2⁽⁴⁾,5-dihydro-[1,2,4]oxadiazole 
• 1769-24-0 2-methyl-4-quinazolone 
• 5692-19-3 N-benzoylacetamidine 
• 93995-91-6 Bis-(1-benzamino-ethyl)-amin 
• 110235-02-4 1,1,1-trifluoro-3-(5-phenyl-1,2,4-oxadiazol-3-yl)propane-2,2-diol 
• 87277-54-1 N-Benzoylacetimidsaeure-ethylester 
• 948027-86-9 (Z)-N-[1-(2,2,3,3-tetramethylaziridin-1-yl)ethylidene]benzamide 
• 1575-95-7 N-acetylbenzamide 
• 55-21-0 benzamide 

Relevant academic research and scientific papers

Beyond direct Nrf2 activation; reinvestigating 1,2,4-oxadiazole scaffold as a master key unlocking the antioxidant cellular machinery for cancer therapy

Harnessing the antioxidant cellular machinery has sparked considerable interest as an efficient anticancer strategy. Activating Nrf2, the master switch of the cellular redox system, suppresses ROS, alleviates oxidative stress, and halts cancer progression

A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes

Various 3,5-disubstituted-1,2,4-oxadiazoles are smoothly formed via copper-catalyzed cascade annulation of amidines and methylarenes. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 1,2,4-oxadiazoles from easily available starting materials, with inexpensive copper catalysts and green oxidants. It has the advantages of atom- and step-economy, good functional group tolerance, as well as operational simplicity.

A metal-free tandem approach to prepare structurally diverse N-heterocycles: Synthesis of 1,2,4-oxadiazoles and pyrimidinones

A metal-free one-pot approach to the diversity oriented synthesis of N-heterocycles, 1,2,4-oxadiazoles and 2,6 disubstituted pyrimidin-4-ones is described via carboxamidation of amidines with aryl carboxylic acids and aryl propargylic acids. The reactions occur at room temperature forming N-acylamidines which undergo tandem nucleophilic addition-deamination- intramolecular cyclisation to give the corresponding heterocyclic compounds in good to excellent yields. This one pot approach has led to the successful synthesis of the drug lead molecule, ataluren, 3-(5-(2-fluorophenyl)-1,2,4- oxadiazol-3-yl) benzoic acid in two steps. the Partner Organisations 2014.

Mild and efficient one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from nitriles mediated by K 3PO 4

Potassium phosphate, K3PO4, has been proved to be a cheap, strong, and efficient reagent for the one-pot synthesis of 3,5-disubstituted-1,2,4-oxadiazoles from nitriles and acid chlorides under mild conditions. [Supplementary material

Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: A highly efficient and fluoride-free ring closure reaction of O-acylamidoximes

Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range of substrates. Additionally, due to the absence of fluoride, TBAH will not result in corrosion of reactor vessels and therefore is better suited for large-scale synthesis.

Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: A highly efficient and fluoride-free ring closure reaction of O-acylamidoximes

Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range of substrates. Additionally, due to the absence of fluoride, TBAH will not result in corrosion of reactor vessels and therefore is better suited for large-scale synthesis.

Reaction of oximes of-diketones with diphosphorous tetraiodide for preparation of oxadiazoles and nitriles

The utility of diphosphorous tetraiodide as a new, mild, condensing agent for synthesis of oxadiazole is described. These data indicate the simple dehydration of oximes to 1,2,5-oxadiazole as well as the rearrangements of oximes to normal Beckmann product 1,2,4-oxadiazole. However, mono-oxime of benzil undergoes abnormal Beckman rearrangement to benzaldehyde as major product. The described method is simple and important for the synthesis of the oxadiazoles as well as for nitriles.

Condensed oxaziridine-mediated [3+2] cycloaddition: Synthesis of polyhetero-bicyclo compounds

Polyhetero-bicyclo compounds were synthesized by a regioselective [3+2]-cycloaddition reaction between stable condensed oxaziridines and alkenes, alkynes, and nitriles. These molecules showed considerable antimicrobial activity against several gram-positive bacteria.

POSITIVE ALLOSTERIC MODULATORS OF THE NICOTINIC ACETYLCHOLINE RECEPTOR

The invention provides compounds of Formula (I). These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals used to treat diseases or conditions in wh

Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst

Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles. Using 0.1 - 1.0 equivalents of TBAF in THF for 1 - 24 h at room temperature, alkanoyl- and aroyloxyamidines were converted in high yield to the corresponding 3,5-disubstituted-1,2,4-oxadiazoles. A variety of R and R′ substituents were investigated.