84832-73-5

Basic information

• Product Name: 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole
• CAS NO: 84832-73-5
• Molecular Formula: C₁₄H₈Br₂N₂O
• Molecular Weight: 380.0341
• Mol File: 84832-73-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 477.2°C at 760 mmHg
• Flash Point: 242.4°C
• Density: 1.714g/cm³
• Vapor Pressure: 8.24E-09mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole(84832-73-5)
• EPA Substance Registry System: 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole(84832-73-5)

Safety Data

• Hazardous Substances Data: 84832-73-5(Hazardous Substances Data)

Usage

General Description

2,5-bis(3-bromophenyl)-1,3,4-oxadiazole, also known as a BPOD, is a chemical compound that belongs to the family of oxadiazole derivatives. 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole is commonly used as a building block in the synthesis of organic electronic materials, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells. BPOD has high thermal stability and good charge transport properties, making it a desirable material for use in electronic devices. It is also known for its ability to emit blue light, making it useful in the development of blue OLEDs. Additionally, BPOD has been studied for its potential application in the field of sensors and optoelectronic devices due to its favorable optical and electronic properties.

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Relevant articles and documents

IBX/KI promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles

Background: Oxadiazoles are privileged scaffolds in different areas of medicinal, pesticidal, polymer and material science. They act as anticancer, benzodiazepine receptor agonists, antimicrobial, analgesic, diuretic and tyrosinase inhibitors etc. A number of compounds containing an oxadiazole moiety are in late stage clinical trials including zibotentan and furamizole. Despite numerous methods are reported, the majority of them suffer from major drawbacks such as the use of strong alkaline or acidic conditions, highly toxic and corrosive reagents and also involve the use of costly reagents, elevated temperatures and longer reaction times. Inspired by the potential application of hypervalent iodonium reagents in organic synthesis, we would like to explore the readily available IBX and KI reagents for the facile synthesis of 1, 3, 4-oxadiazoles. Method: Oxidative cyclization has successfully been developed for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles. Results: An efficient process for the one-pot synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles has been developed using IBX/KI system at 25°C. The reaction was successful with a wide range of substrates such as aromatic and heterocyclic aldehyde and arylhydrazides to afford the corresponding unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles. The mild reaction conditions, cost-effective reagents and short reaction time are noteworthy advantages of this methodology. Conclusion: We have developed a one-pot strategy for the synthesis of 1, 3, 4-oxadiazioles using a combination of IBX/KI at ambient temperature. This one-pot procedure proved to be quite general and worked well with a wide variety of aryl and heterocyclic aldehydes and variety of acylhydrazides. The advantage of this method lies in the simplicity of experimental procedure and the ready accessibility of the reagents, which render this, an experimentally attractive method for the preparation of unsymmetrical 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.

The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics

An understanding of the structure-function relationships of conjugated polymers is an invaluable resource for the successful design of new materials for use in organic electronics. To this end, we report the synthesis, characterisation and optoelectronic properties of a range of new alternating copolymers of dibenzosilole. Suzuki polycondensation reactions were used to afford a series of eight conjugated materials by the respective combination of either a 3,6- or 2,7-linked 9,9-dioctyldibenzosilole with 3,6-linked-N- octylcarbazole, triarylamine, oxadiazole and triazole monomers. The copolymers were fully characterised using 1H, 13C{1H} NMR spectroscopy, size exclusion chromatography (SEC), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The photophysical properties were determined using UV-Vis spectroscopy, photoluminescence (PL) measurements, cyclic voltammetry (CV) and photoelectron emission spectroscopy in air (PESA). The spectroscopic and electrochemical measurements were used to determine the materials' HOMO and LUMO energies and the values were correlated with the copolymer composition and structure. A selection of the copolymers (P4, P5 and P8) were evaluated as the active layer within single-layer polymer light emitting diodes (PLEDs), with the configuration: glass/ITO/PEDOT:PSS/emissive layer/Ba/Al, which gave low intensity electroluminescence. The selected copolymers were also evaluated as the organic semiconductor in bottom-gate, bottom-contact organic field effect transistors (OFETs). The best performing devices gave a maximum mobility of 3 × 10-4 cm2 V-1 s-1 and on/off current ratios of 105. The Royal Society of Chemistry 2011.