1044-49-1

Usage

Uses

Used in Chemical and Biological Assays:
2,5-BIS(4-NITROPHENYL)-1,3,4-OXADIAZOLE is used as a fluorescent material for its ability to emit light upon excitation, which is crucial in the detection and analysis of various chemical and biological processes.
Used in Organic Optoelectronic Devices:
2,5-BIS(4-NITROPHENYL)-1,3,4-OXADIAZOLE is used as a component in the development of high-performance organic optoelectronic devices due to its high thermal stability, which contributes to the device's performance and longevity.
Used in Materials Science and Technology:
2,5-BIS(4-NITROPHENYL)-1,3,4-OXADIAZOLE is used as a potential precursor in the synthesis of novel conjugated materials and dyes, where its unique properties can be leveraged to create innovative materials with specific characteristics for various applications in the field of materials science and technology.

InChI:InChI=1/C14H8N4O5/c19-17(20)11-5-1-9(2-6-11)13-15-16-14(23-13)10-3-7-12(8-4-10)18(21)22/h1-8H

Upstream product

• 4402-22-6 N,N'-bis-(4-nitro-benzoyl)-hydrazine 
• 122-04-3 4-nitro-benzoyl chloride 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 16687-60-8 5-(4-nitrophenyl)-2H-tetrazole 
• 28115-92-6 4-nitrobenzoyl isothiocyanate 
• 93-97-0 benzoic acid anhydride 
• 51771-32-5 4-Nitro-benzoic acid [1-(4-nitro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 555-16-8 4-nitrobenzaldehdye 
• 62-23-7 4-nitro-benzoic acid 
• 4231-71-4 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 1090-82-0 2-(4-nitrophenyl)-5-phenyl-1,3,4-oxadiazole 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 

Downstream Products

• 92061-22-8 2-(4-aminophenyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole 
• 2425-95-8 2,5-bis(p-aminophenyl)-1,3,4-oxadiazole 

Relevant academic research and scientific papers

A new synthesis of symmetrical 2,5-disubstituted 1,3,4- oxadiazoles

Several new 2,5-disubstituted 1,3,4-oxadiazoles have been synthesized in good yields by reaction of aromatic acids with hydrazine dihydrochloride in a mixture of orthophosphoric acid, phosphorus pentoxide and, in general, with addition of phosphorus oxychloride to the reaction mixture. The structures of new oxadiazoles derivatives were confirmed by analytical and spectral data.

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, Characterization and Energetic Properties of 1,3,4-Oxadiazoles

An efficient cyclization between nitro-substituted benzoic acids and nitro-substituted benzohydrazides affords 1,3,4-oxadiazoles. Facile synthesis and a broad substrate scope produce a range of compounds, some of them with potential as high-energy compounds. Heats of formation (ΔHf) and densities (ρ) were calculated, and heats of decomposition (ΔHd) and combustion (ΔHc) were determined experimentally. The densities of seven of the synthesized compounds were determined by gas pycnometry, and the respective values of detonation velocity (VD), detonation pressure (PD) and specific impulse (ISP) were calculated using the EXPLO5 program. An X-ray structure of 2-(2,4-dinitrophenyl)-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole (4n) revealed the non-planarity of the molecule and afforded a crystal density of 1.698 (at 120 K), close to the pycnometric value of 1.64 at room temperature. Efficient cyclization between nitro-substituted benzohydrazides and nitro-substituted benzoic acids affords energetic 1,3,4-oxadiazoles.

Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

A convenient, efficient and one-pot synthesis of chemically and pharmaceutically interesting symmetrical-2,5-disubstituted-1,3,4-oxadiazoles is reported. The protocol involves anodic oxidation of aldehyde-N-arylhydrazones in anhyd. MeCN-LiClO4. Constant potential electrolysis carried out in an undivided cell and platinum electrodes leads to the formation of the corresponding oxadiazoles under ambient condition and the mechanism was deduced from voltammetry studies. The reaction proceeded smoothly with high atom economy. Springer Science+Business Media Dordrecht 2013.

17O NMR studies of substituted 1,3,4-oxadiazoles

Three series of substituted 1,3,4-oxadiazoles were studied by 17O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.

A new synthesis of 1,3,4-oxadiazoles. Cyclization of N,N'- diacylhydrazines catalyzed by palladium(0)

Several 1,3,4-oxadiazoles were synthetized by cyclization of N,N'- diacylhydrazines catalyzed by palladium(0). Water formed during the reaction is responsible for the hydrolysis of the products. To avoid it, we introduced benzoic anhydride into the medium and obtained an increased yield of oxadiazoles.

Research in the 2,5-Diaryl-1,3,4-oxadiazole Series. 1. Electronic Structures and Spectral-Luminescence Properties of Substituted 2,5-Diphenyl-1,3,4-oxadiazoles

The dependence of the spectral-luminescence properties of substituted 2,5-diphenyl-1,3,4-oxadiazoles on the electronic nature of the substituents was studied.Experimental and theoretical studies confirm the electron-acceptor character of the oxadiazole ring and constitute evidence for the rather effective transmission of the electronic effects through the heteroring.

REACTIONS OF BENZOYL ISOTHIOCYANATES WITH 5-SUBSTITUTED TETRAZOLES

A method of preparing 2,5-disubstituted 1,3,4-oxadiazoles from benzoyl isothiocyanates and 5-substituted tetrazoles is described.The transformation of the tetrazole into a 1,3,4-oxadiazole ring takes place readily under neutral conditions giving high yields of the desired products.