2491-89-6

Usage

Uses

Used in Organic Synthesis:
2,5-BIS(3-NITROPHENYL)-1,3,4-OXADIAZOLE is used as a reagent in organic synthesis for its ability to contribute to the formation of complex organic molecules, leveraging its structural and chemical properties.
Used in Dye and Pigment Production:
In the dye and pigment industry, 2,5-BIS(3-NITROPHENYL)-1,3,4-OXADIAZOLE is used as a component in the production of various dyes and pigments, capitalizing on its bright yellow coloration.
Used in Pharmaceutical Manufacturing:
2,5-BIS(3-NITROPHENYL)-1,3,4-OXADIAZOLE is utilized in the manufacturing of pharmaceuticals, where its chemical properties may contribute to the development of new drugs or improve the synthesis process of existing ones.
Used in Materials Science:
In the field of materials science, 2,5-BIS(3-NITROPHENYL)-1,3,4-OXADIAZOLE is used for its fluorescent properties, making it a potential component in the development of organic light-emitting diodes (OLEDs), which are used in various display and lighting applications.
Safety Considerations:
Due to the explosive nature of 2,5-BIS(3-NITROPHENYL)-1,3,4-OXADIAZOLE, it should be handled with extreme care and caution to prevent accidents and ensure the safety of personnel and equipment.

Upstream product

• 5509-89-7 (m-nitrobenzoyl)hydrazine 
• 1874-38-0 2-(3-nitrophenyl)-5-phenyl-1,3,4-oxadiazole 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 
• 618-94-0 3-nitrobenzoic acid hydrazide 
• 121-92-6 3-nitrobenzoic acid 
• 302813-25-8 C₁₄H₁₀N₄O₅ 
• 606-26-8 o-nitrobenzohydrazide 
• 552-89-6 2-nitro-benzaldehyde 
• 121-90-4 m-nitrobenzoic acid chloride 

Downstream Products

• 2588-85-4 2,5-bis(3-aminophenyl)[1,3,4]-oxadiazole 
• 92906-07-5 3-[5-(3-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-aniline 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 

Relevant academic research and scientific papers

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.

Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents

The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis. The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4-oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds. The Royal Society of Chemistry 2013.

Formation of exciplexes in films of polyimides, polyamides, and polyquinazolones derived from aromatic and heteroaromatic diamines

The emission bands exchibited by films of polyimides derived from 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride, hexafluoroisopropylidenedibenzene-3,3′,4,4′-tetracarboxylic dianhydride, and aromatic and heteroaromatic diamines, and also of polyamides and polyquinazolones derived from the same amines are exciplex bahnds. With polyamides, complexes in the ground state are formed. The fluorescence of the photoconductivity sensitizer Rhodamine 6G is quenched in films of these polymers by the exciplex mechanism. 2005 Pleiades Publishing, Inc.

An efficient one pot synthesis of 1,3,4-oxadiazoles

Various 1,3,4-oxadiazoles have been synthesized in excellent yields by BF3·Et2O promoted cyclodehydration of 1,2-diacyl and diaroyl hydrazines prepared in situ from corresponding acid chlorides and hydrazine.

Substitution Reactions of Phenylated Aza-heterocycles. Part 1. Nitration of 2,5-Diphenyl-1,3,4-oxadiazole: a Product Study using High Performance Liquid Chromatography

Contrary to a previous literature report, nitration of 2,5-diphenyl-1,3,4-oxadiazole (1) under various conditions gives a mixture of all six possible 2,5-bisnitrophenyl derivatives, which may be analysed quantitatively using high performance liquid chromatography.Nitration using nitric acid alone gives mainly the three isomers with p-nitrophenyl groups, i.e. (7), (9), and (10), whereas mixed acids and nitronium tetrafluoroborate give mainly meta-nitration products, i.e. (6), (8), and (9).Nitration of the three 2-(nitrophenyl)-5-phenyl-1,3,4-oxadiazoles also shows considerable variation of product ratio according to the conditions.