847-39-2

Usage

Uses

Used in Organic Electronics and Optoelectronics:
2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole is utilized as a building block in the synthesis of light-emitting materials and organic semiconductors. Its role in these applications is crucial for the development of advanced technologies such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells, where its electronic and optical properties are harnessed for improved performance.
Used in Medicinal Chemistry:
2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole also holds potential in the field of medicinal chemistry due to its diverse biological activities. The exploration of 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole for its therapeutic potential is an ongoing area of research, with the aim of discovering new pharmaceutical agents that can benefit from its unique properties.

InChI:InChI=1/C16H14N2O3/c1-19-13-7-3-11(4-8-13)15-17-18-16(21-15)12-5-9-14(20-2)10-6-12/h3-10H,1-2H3

Upstream product

• 849-82-1 N,N'-bis-(4-methoxybenzoyl)hydrazine 
• 51771-21-2 4-methoxy-N'-[(4-methoxyphenyl)methylidene]benzohydrazide 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 100-09-4 4-methoxybenzoic acid 
• 132500-88-0 C₂₀H₂₂N₄O₆ 
• 155164-68-4 4,5-Dichloro-2-(4-methoxy-benzoyl)-2H-pyridazin-3-one 
• 41097-47-6 N,N'-Bis-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazine 
• 100-07-2 4-methoxy-benzoyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 829-35-6 2-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 696-62-8 para-iodoanisole 
• 121-98-2 methyl 4-methoxybenzoate 
• 33708-60-0 4-methoxy-benzaldehyde-(4-methoxy-benzylhydrazone) 
• 140-69-2 4-methoxybenzylhydrazine 

Downstream Products

• 10600-83-6 2,5-bis-(4-hydroxyphenyl)-1,3,4-oxadiazole 
• 1252660-25-5 2-(4-methoxyphenyl)-5-(4-hydroxyphenyl)-[1,3,4]oxadiazole 
• 842-79-5 2-(4-methoxy-phenyl)-5-phenyl-[1,3,4]oxadiazole 

Relevant academic research and scientific papers

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.

One pot solvent-free solid state synthesis, photophysical properties and crystal structure of substituted azole derivatives

A solvent-free solid state method has been developed to synthesize three series of substituted azole derivatives (including 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole) in high yields by condensation cyclization of N,N′-bishydrazide derivatives with corresponding cyclization agents, respectively. This general method avoids the use of organic solvents, saves cost and resources, simplifies post-processing and increases reaction rates. These compounds have been fully characterized by 1H NMR, 13C NMR, elemental analysis and MS. The structure of 2,5-di (4-tertbutylphenyl)-1,3,4-oxadiazole has been determined by single crystal X-ray diffraction analysis. The cell parameters are as follows: monoclinic crystal system, Cc space group, a = 18.735 (2) ?, b = 6.3375 (8) ?, c = 16.824 (2) ? and α = γ = 90°; β = 98.292 (2). The electronic absorption and fluorescent properties of these compounds have been systematically investigated for the first time. The relationships between heterocyclic structures and photophysical properties have been discussed. The alteration of emission and absorption wavelengths can be elucidated by hybrid atoms' electronegativity and Substituents' Hammett constants. This approach proposes a novel insight to provide a great number of novel substituted azole derivatives with good photophysical properties by a general green method.

Synthesis method of 2,5-disubstituted-1,3,4-oxadiazole

The invention discloses a synthesis method of a drug intermediate, namely, 2,5-disubstituted-1,3,4-oxadiazole. 2,5-disubstituted-1,3,4-oxadiazole is synthesized with a one-pot method under the photocatalytic action with simple hydrazide compounds as raw materials. 2,5-disubstituted-1,3,4-oxadiazole can be produced through a reaction at the room temperature with a common halogen lamp as a light source, eosinY as a catalyst, potassium carbonate as an additive and ethanol as a solvent. The method has the characteristics that the raw material source is simple, the reaction condition is mild and the like.

Synthesis, liquid-crystalline, photophysical and chemosensor properties of oxadiazole/thiadiazole-based amphiphiles with glycerol groups

Two series of heterocycle-based mesogens consisting of a long 2,5-diphenyl-1,3,4-oxadiazole/thiadiazole rigid core with three lipophilic and flexible alkyl chains at one end and a polar glycerol group at the opposite end have been synthesized via one pot cyclization reaction. These compounds were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), X-ray scattering, cyclic voltammetry, UV–vis spectroscopy and photoluminescence measurements. Upon elongation of the alkyl chains, a transition from hexagonal columnar phase to Pm3ˉn-type cubic phase was observed in both series. Oxadiazole series are blue luminescent LCs with binding selectivity to Li+, while thiadiazole series are blue-green luminescent LCs with binding selectivity to Fe3+.

The effects of asymmetric bent-shaped compounds on the temperature range and electro-optical performances of liquid crystalline blue phases

A series of asymmetric and symmetric bent-shaped molecules with branched terminals were synthesized and characterized. Their effects on inducing blue phase and electro-optical performances were compared and analyzed experimentally. It was found that the asymmetric and symmetric compounds almost have the same effect on inducing and stabilizing blue phase, but the electro-optical performance of mixtures doped with asymmetric compounds are much better than that of mixtures doped with symmetric compounds for they have a totally different dielectric anisotropy which can contribute to a larger Kerr constant.

Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4-Oxadiazole/1,3,4-Oxadiazoline and 1,2,4-Triazole Derivatives from N-Substituted Hydrazides

A metal-free method for the synthesis of substituted 1,3,4-oxadiazole/1,3,4-oxadiazoline and 1,2,4-triazole derivatives from a common starting material via reagent/substituent switching is reported. In the presence of 2-fluoropyridine/triflic anhydride, 1,3,4-oxadiazole derivatives were exclusively formed from N′-tert-butylhydrazides and 1,3,4-oxadiazoline derivatives were produced from N-phenylhydrazides. On the other hand, when using pyridine/triflic anhydride, salts of 1,2,4-triazoles were the sole products. (Figure presented.).

Symmetrical and non-symmetrical 2,5-diaryl-1,3,4-oxadiazoles: Synthesis and photophysical properties

We report herein the synthesis of 2,5-diaryl-1,3,4-oxadiazoles containing both electron-donating and withdrawing substituents as well as bis- and tris-2,5-disubstituted-1,3,4-oxadiazoles containing electron-donating substituents. The photophysical properties of the synthesized compounds were studied using UV-Vis and fluorescence spectroscopy. The aryl substitution pattern was found to have a marked impact on both luminescence efficiency and other photophysical properties. An increase in the number of electron-donating groups and/or the number of heterocyclic rings provided a red shift of the emission maxima, as well as an increase of the Stokes shifts. The same effect was observed for mono-1,3,4-oxadiazoles containing push-pull substituents on the aryl rings.

Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source

A palladium-catalyzed aminocarbonylation reaction of aryl halides with chloroform and tetrazoles has been developed, where chloroform was employed as the carbon monoxide (CO) source in the presence of cesium hydroxide. The in situ generated N-acylated tetrazoles were unstable and easily decomposed to afford 2,5-disubstituted 1,3,4-oxadiazoles. A wide range of tetrazoles and aryl halides reacted smoothly under the optimized reaction conditions to give the corresponding products in moderate to good yields.

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

A metal- and base-free protocol for one-pot synthesis of 2,5-diaryl 1,3,4-oxadiazoles via a radical-promoted cross-dehydrogenative coupling strategy was developed. This reaction involved the N-acylation of aryl tetrazoles with aryl aldehydes, followed by thermal rearrangement. A wide range of aryl tetrazoles and aryl aldehydes survived the reaction conditions to deliver the corresponding products in moderate to good yields. (Chemical Equation Presented).