1874-47-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(4-Methylphenyl)-5-phenyl-1,3,4-oxadiazole is used as a building block for the synthesis of various pharmaceuticals due to its unique chemical properties that can enhance the efficacy and stability of the resulting compounds.
Used in Agrochemical Synthesis:
In the agrochemical industry, MPPO is utilized as a building block for the development of new agrochemicals, leveraging its chemical properties to improve the performance of these products in agricultural applications.
Used as a Fluorescent Dye:
2-(4-Methylphenyl)-5-phenyl-1,3,4-oxadiazole is used as a fluorescent dye in research and diagnostic applications, taking advantage of its fluorescent properties to aid in the visualization and detection of certain substances.
Used as a Sensor for Heavy Metal Ions:
MPPO is employed as a sensor for detecting heavy metal ions, capitalizing on its ability to interact with these ions and provide a measurable response, which is crucial for environmental monitoring and safety assessments.
Used in Environmental Monitoring:
2-(4-Methylphenyl)-5-phenyl-1,3,4-oxadiazole is used in environmental monitoring applications to detect and measure the presence of heavy metal ions, contributing to the assessment of environmental safety and污染 control.
Used in Material Science:
In the field of material science, MPPO is used as a component in the development of new materials, where its chemical and fluorescent properties can contribute to the creation of advanced materials with specific properties for various applications.

InChI:InChI=1/C15H12N2O/c1-11-7-9-13(10-8-11)15-17-16-14(18-15)12-5-3-2-4-6-12/h2-10H,1H3

Upstream product

• 98-88-4 benzoyl chloride 
• 24994-04-5 5-(4-methylphenyl)-2H-tetrazole 
• 874-60-2 4-methyl-benzoyl chloride 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 59635-52-8 N-(phenylsulfonyl)benzohydrazonoyl chloride 
• 3619-22-5 p-toluic hydrazide 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 613-94-5 benzoic acid hydrazide 
• 99-94-5 p-Toluic acid 
• 13222-85-0 p-methylbenzoic anhydride 
• 93-97-0 benzoic acid anhydride 
• 1530-73-0 4-methyl-N'-(4-methylbenzoyl)benzohydrazide 
• 825-56-9 2-phenyl-1,3,4-oxadiazole 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 72094-02-1 5-phenyl-3-{4-[4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-trans-styryl]-phenyl}-[1,2,4]oxadiazole 
• 72094-03-2 5-(4-chloro-phenyl)-3-{4-[4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-trans-styryl]-phenyl}-[1,2,4]oxadiazole 
• 72094-04-3 5-(4-methoxy-phenyl)-3-{4-[4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-trans-styryl]-phenyl}-[1,2,4]oxadiazole 
• 53349-77-2 2-phenyl-5-{4-[trans-2-(2-phenyl-benzofuran-6-yl)-vinyl]-phenyl}-[1,3,4]oxadiazole 
• 16157-23-6 2-[4-(trans-2-biphenyl-4-yl-vinyl)-phenyl]-5-phenyl-[1,3,4]oxadiazole 
• 16157-27-0 2-[4-(trans-2-naphthalen-1-yl-vinyl)-phenyl]-5-phenyl-[1,3,4]oxadiazole 
• 16157-30-5 2-[4-(trans-2-naphthalen-2-yl-vinyl)-phenyl]-5-phenyl-[1,3,4]oxadiazole 
• 68087-31-0 2-phenyl-5-[4-((E)-styryl)phenyl][1,3,4]oxadiazole 
• 37421-31-1 2-phenyl-7-{4-[4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-trans-styryl]-phenyl}-2,7-dihydro-benzo[1,2-d;3,4-d']bis[1,2,3]triazole 
• 53349-71-6 2-phenyl-5-[4-(4-trans-styryl-trans-styryl)-phenyl]-[1,3,4]oxadiazole 
• 53349-74-9 2-[4-(4-benzofuran-2-yl-trans-styryl)-phenyl]-5-phenyl-[1,3,4]oxadiazole 
• 16157-17-8 2-[4-(4-chloro-trans-styryl)-phenyl]-5-phenyl-[1,3,4]oxadiazole 
• 59098-58-7 2-{4-[2-(5-methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-5-phenyl-[1,3,4]oxadiazole 
• 59098-67-8 2-{4-[2-(2,5-diphenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-5-phenyl-[1,3,4]oxadiazole 

Relevant academic research and scientific papers

Halogen bonding two-point recognition with terphenyl derivatives

Two-point recognition involving neutral terphenyl-based halogen bond donors (halogen-based Lewis acids) was investigated. Oxadiazole and pyridazole derivatives were identified by DFT as suitable binding partners, even though gas-phase binding was weak. X-

A novel 1-D coordination polymer constructed from disilver-1,3,4-oxadiazole nodes and perchlorato bridges

The reaction of silver perchlorate with 2-phenyl-5-(p-tolyl)-1,3,4-oxadiazole (L) affords a 1-D coordination polymer, [Ag3L4(ClO4)3] (1). Two silver ions are bridged by two L ligands, through the nitrogen atoms of the oxadiazole ring, resulting in binuclear units. The coordination polymer is constructed from binuclear nodes, {Ag2L2}, connected by perchlorato bridges. The investigation of the optical properties of compound 1 indicates a slight change in the emission profile compared to the organic ligand, showing blue luminescence upon excitation at λ?=?300?nm.

The preparation, characterization and catalytic activity of Ni NPs supported on porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide)

Herein, we report the synthesis of nickel nanoparticles under mild conditions using porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide) as a protecting/stabilizing agent and sodium borohydride as a reducing agent. The porous cross-linked polymeric support was preparedviacombining the use of sol-gel, nanocasting, and crosslinking techniques, in which thep-styrene sulfonamide monomer (PSSA) andN,N′-methylene-bis (acrylamide) (MBA) cross-linker underwent copolymerization on the surface of sodium alginate in the presence of a SiO2nanoparticle (NP) template (Alg-PSSA-co-ACA). The prepared catalyst (Alg-PSSA-co-ACA@Ni) showed high catalytic activity for the one-step synthesis of 1,3,4-oxadiazoles from the reaction of hydrazides and aryl iodides through isocyanide insertion/cyclization.

Reusable colorimetric and fluorescent chemosensors based on 1,8-naphthalimide derivatives for fluoride ion detection

Two 1, 8-naphthalimide derivatives, 2-(2-ethylhexyl)-6-(2-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzylidene)hydrazinyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (named as NAOZ) and 2-(2-ethylhexyl)-6-(2-(4-(5-phenyl-1,3,4-thiadiazol-2-yl)benzylidene)hydrazinyl)

Experimental and Theoretical Studies on the Mechanism of DDQ-Mediated Oxidative Cyclization of N-Aroylhydrazones

The controversial single-electron-transfer process, frequently proposed in many 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated reactions, was investigated experimentally and theoretically using the oxidative cyclization of aroylhydrazone with DDQ. DDQ-mediated oxadiazole formation involves several processes, including cyclization to form an oxadiazole ring and N-H bond cleavage, either by proton, hydride, or hydrogen atom transfer. The detailed mechanistic study using the M06-2X density functional theory, and the 6-31+G(d,p) basis set, suggests that the pathways involving radical ion pair (RIP) intermediates, which resulted from single-electron transfer (SET), were found to be energetically nearly identical to the pathway without the SET. The substituent-dependent reactivity of oxadiazole formation was consistent with the free energy profiles of both pathways, with or without the SET. This result indicates that in addition to the electron-transfer pathway, the nucleophilic addition/elimination pathway for DDQ should be considered as a possible mechanism of the oxidative transformation reaction using DDQ.

UV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow

A range of 1,3,4-oxadiazoles have been synthesized using a UV-B activated flow approach starting from carboxylic acids and 5-substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids.

Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions

1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Harnessing Autoxidation of Aldehydes: In Situ Iodoarene Catalyzed Synthesis of Substituted 1,3,4-Oxadiazole, in the Presence of Molecular Oxygen

Isobutyraldehyde underwent auto-oxidation in the presence of molecular oxygen to generate an acyloxy radical under a "metal-free" environment. They were subsequently exploited in situ to afford hypervalent iodines with p-anisolyl iodide which generated substituted 1,3,4-oxadiazoles in moderate to excellent yields from N′-arylidene acetohydrazides. The reaction strategy tolerated diverse substitution on the hydrazide substrates. Control experiments and literature precedence supported the formation of an in situ iodosylarene complex that facilitates the formation of products.

Mixed N-heterocycles/N-heterocyclic carbene palladium(II) allyl complexes as precatalysts for direct arylation of azoles with aryl bromides

A series of mixed N-heterocycles/N-heterocyclic carbene palladium(II) allyl complexes with general formula [(NHC)Pd(η3-allyl)]2(μ2-N-heterocycles)(BF4)2 were prepared in one pot based on anion metathesis of (NHC)Pd(η3-allyl)Cl complexes and then ligand replacement with N-heterocycles [N-heterocycles = pyrazine (pyz), 4,4′-bipyridine (bpy) and trans-4,4′-bipyridylethylene (bpe)]. The solid-state structures shown dinuclear structures with two palladium(II) centers holding together by bridged N-heterocycles. Initially investigation of the obtained complexes as precatalysts for direct C[sbnd]H bond arylation of azoles with aryl bromides was carried out.