313662-94-1

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 50907-23-8 5-(4-bromophenyl)-1H-tetrazole 
• 100-07-2 4-methoxy-benzoyl chloride 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 100-09-4 4-methoxybenzoic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-76-5 4-Bromobenzoic acid 
• 5933-32-4 4-bromobenzoic acid hydrazide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 829-35-6 2-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 1613331-40-0 2-(4-(anthracen-9-yl)phenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole 

Relevant academic research and scientific papers

In situ generated cetyltrimethylammonium bisulphate in choline chloride-urea deep eutectic solvent: A novel catalytic system for one pot synthesis of 1,3,4-oxadiazole

Cetyltrimethylammonium bisulphate ([CTA]HSO4) catalysed one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles from carboxylic acid and acid hydrazide in biodegradable deep eutectic solvent is investigated. [CTA]HSO 4 is generated in situ from cetyltrimethylammonium peroxodisulphate. Cyclization of diacylhydrazide using [CTA]HSO4 gives best alternative to traditional dehydration agents. Its remarkable features include a milder procedure, simplicity in workup and purification, good to excellent yields of products, use of inexpensive, recyclable reagents, and eco-friendly aspects by avoiding toxic catalysts/reagents and solvents. Graphical Abstract: [Figure not available: see fulltext.].

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.

Synthesis of New Alkynyl-Bridged 2,5-Disubstituted 1,3,4-Oxadiazoles

A synthesis of new alkynyl-derived 2,5-disubstituted 1,3,4-oxadiazoles through palladium/copper-catalyzed Sonogashira cross-coupling between oxadiazole-substituted phenyl bromides and various arylacetylenes is described. Investigation of the absorption and emission spectra of the target compounds indicates emission profiles in the near-blue and blue region and high luminescence intensities. The presented approach is very convenient for the synthesis of luminescent small-molecules or precursors of other complex derivatives that are useful in the preparation of OLEDs as electron-transporting components.

Synthesis of new 1,3,4-oxadiazoles by oxidative cyclisation with bis(trifluoroacetoxy)iodobenzene

2,5-Diaryl-1,3,4-oxadiazoles are valuable molecules mainly in the construction of Organic Light Emitting Diodes (OLEDs) due to their electron deficient character. More recently, unsymmetrical 2,5- disubstituted compounds found important applications as fluorescent sensor for various ions. We describe herein synthesis of new 2,5-diaryl-1,3,4-oxadiazoles having as intermediates N-acylhydrazones, readily available through the condensation reaction between aldehydes and hydrazides. The oxadiazole ring was formed by oxidative cyclisation using hypervalent iodine reagents, particularly, bis(trifluoroacetoxy)iodobenzene, which acts as a mild and convenient reagent for the synthesis of this type of unsymmetrical heterocyclic compounds. All synthesized compounds were fully characterized by NMR and MS measurements to confirm their purity and identity.

Design and synthesis of novel anthracene derivatives as n-type emitters for electroluminescent devices: A combined experimental and DFT study

Six novel anthracene-oxadiazole derivatives, 4a (2-(4-(anthracen-9-yl) phenyl)-5-p-tolyl-1,3,4-oxadiazole), 4b (2-(4-(anthracen-9-yl)phenyl)-5-(4-tert- butylphenyl)-1,3,4-oxadiazole), 4c (2-(4-(anthracen-9-yl)phenyl)-5-(4- methoxyphenyl)-1,3,4-oxadiazole), 8a (2-(4-(anthracen-9-yl)phenyl)-5-m-tolyl-1, 3,4-oxadiazole), 8b (2-(3-(anthracen-9-yl)phenyl)-5-(4-tert-butylphenyl)-1,3,4- oxadiazole) and 8c (2-(3-(anthracen-9-yl)phenyl)-5-(3,4,5-trimethoxyphenyl)-1,3, 4-oxadiazole) have been synthesized and characterized for use as emitters in organic light emitting devices (OLEDs). They show good thermal stability (T d, 297-364 °C) and glass transition temperatures (Tg) in the range of 82-98 °C, as seen from the thermo gravimetric analysis and differential scanning calorimetric studies. The solvatochromism phenomenon and electrochemical properties have been studied in detail using UV-Vis absorption, fluorescence spectroscopy and cyclic voltammetry. TD-DFT calculations have been carried out to understand the electrochemical and photophysical properties. The spatial structures of 4b and 8c are further confirmed by X-ray diffraction analysis. Un-optimized non-doped electroluminescent devices were fabricated using these anthracene derivatives as emitters with the following device configuration: ITO (120 nm)/α-NPD (30 nm)/4a-4c or 8a-8c (35 nm)/BCP (6 nm)/Alq3 (28 nm)/LiF (1 nm)/Al (150 nm). Among all the six compounds, 8a displays the maximum brightness of 1728 cd m-2 and current efficiency 0.89 cd A-1. Furthermore, as an electron transporter, 8a exhibited superior performance (current efficiency is 11.7 cd A-1) than the device using standard Alq3 (current efficiency is 8.69 cd A-1), demonstrating its high potential for employment in OLEDs. These results indicate that the new anthracene-oxadiazole derivatives could play an important role in the development of OLEDs. The Royal Society of Chemistry and Owner Societies.

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.

Copper-mediated direct arylation of 1,3,4-oxadiazoles and 1,2,4-triazoles with aryl iodides

The copper-mediated direct arylation of 1,3,4-oxadiazoles and 1,2,4-triazoles with aryl iodides proceeds efficiently in the presence of suitable ligands and bases. This method allows the installation of a variety of aryl moieties bearing a functional group such as ketone, ester, or nitrile so as to enable the facile construction of various functionalized oxadiazole and triazole core π systems.

Oxidative cyclization of aromatic aldehyde n-acylhydrazones by bis(trifluoroacetoxy)iodobenzene

Aromatic aldehyde N-acylhydrazones were oxidized into 2,5-disubstituted 1,3,4-oxadiazoles with bis(trifluoroacetoxy)iodobenzene in CHCl3 or DMSO at room temperature in good to excellent yields. Copyright Taylor & Francis Group, LLC.