2425-95-8

Usage

Uses

Used in Polymer Synthesis:
BAO is used as a monomer in the synthesis of aromatic polyimides. The expression is: 2,5-BIS(4-AMINOPHENYL)-1,3,4-OXADIAZOLE is used as a monomer for the production of aromatic polyimides through high-temperature polycondensation.
Used in Neuroscience Research:
In the field of neuroscience, BAO is used as a reagent for Schiff-type staining of DNA obtained from cerebral cortex neurons. The expression is: 2,5-BIS(4-AMINOPHENYL)-1,3,4-OXADIAZOLE is used as a reagent for Schiff-type staining of DNA for [application reason] to visualize and study the DNA structure in neurons.
Used in Cytofluorometry:
BAO is also utilized in cytofluorometric staining to estimate the nuclear DNA in living and preserved algae. The expression is: 2,5-BIS(4-AMINOPHENYL)-1,3,4-OXADIAZOLE is used as a staining agent for cytofluorometric analysis to estimate the nuclear DNA content in living and preserved algae.
Used in Chemical Industry:
In the chemical industry, BAO is used as a building block for the development of various chemical compounds and materials due to its rigid bidentate ligand structure. The expression is: 2,5-BIS(4-AMINOPHENYL)-1,3,4-OXADIAZOLE is used as a building block for the development of chemical compounds and materials for [application reason] to create new materials with specific properties.

Purification Methods

BAO is recrystallised from EtOH using charcoal and under N2 to avoid oxidation. It is a fluorescent stain for DNA [Yataghanas et al. Exptl Cell Res 56 59 1969]. [Beilstein 27 III/IV 8158.]

Upstream product

• 1044-49-1 bis-(4-nitro-phenyl)-[1,3,4]oxadiazole 
• 16106-38-0 4-aminobenzoyl chloride 
• 150-13-0 4-amino-benzoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 1419388-30-9 C₁₄H₁₄N₄O 
• 556-18-3 4-aminobenzaldehyde 
• 5351-17-7 4-aminobenzohydrazide 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 329317-97-7 2,5-bis(4-trifluoromethylsulfonamidophenyl)-(1,3,4)oxadiazole 
• 1256253-99-2 (Z)-4,4'-(2,5-diphenylene-1,3,4-oxadiazolyl)bis{3-[1-(2,5-dimethyl-3-thienyl)ethylidene]-4-iso-propylidene-pyrrolidine-2,5-dione} 
• 1313751-06-2 C₃₄H₄₂N₆O₇ 
• 1313743-91-7 (2S,2'S)-N,N'-(1,3,4-oxadiazole-2,5-diyldi-4,1-phenylene)bis[1-(phenylacetyl)-2-pyrrolidinecarboxamide] 

Relevant academic research and scientific papers

Bent Shaped 1,3,4-Oxadiazole/Thiadiazole heterocyclic rings containing liquid crystals

Two series of bent shaped 1,3,4-oxadiazole/thiadiazole heterocyclic ring containing liquid crystalline (LC) compounds were synthesized and characterized by FT-IR, 1H, 13C-NMR and ESI-Mass spectroscopic techniques. Liquid crystal properties were investigated by polarized optical microscopy and differential scanning calorimetry. All the compounds exhibited mesophases such as nematic, smectic A and smectic C phases. The liquid crystalline effects were ascertained by changing the central atom in the heterocyclic ring and by increasing the length of the terminal alkyloxy chains which bring considerable improvements on the mesomorphic properties. The absorption and emission spectral studies of all the compounds were investigated and confirmed.

Synthesis and photophysical study of some new highly thermostable blue fluorescent poly(1,3,4-oxadiazole-imide)s containing dimethylamine groups

New poly(1,3,4-oxadiazole-imide)s were synthesized from a diamine containing 1,3,4-oxadiazole ring, 4,4′-diamino-4″-[(2-(4-phenoxy)-5-(4-dimethylaminophenyl)-1,3,4-oxadiazole]triphenylmethane, and different aromatic dianhydrides: 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, 9,9-bis[(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride, 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic anhydride) and perylene-3,4,9,10-tetracarboxylic dianhydride. The polymers were easily soluble in polar organic solvents and exhibited high thermal stability, having 5% weight loss in the range of 445-470 °C and glass transition temperature in the domain of 201-244 °C. The optical properties were investigated in different media. The absorption characteristics (intensity, absorption maximum and shape) of investigated compounds depended on their chemical structures and the nature of environment. The emission of these samples was represented by one broadened and blue emission band. The largest and solvent dependent Stokes shifts values were obtained. The fluorescence quantum yield (QY) values of polymer with hexafluoroisopropylidene groups, in tetrahydrofuran solution, depended on the wavelength used for excitation. This is an exception from Kasha's rule and Vavilov's law, which was attributed either to photodecomposition or to the enhancement of intramolecular energy transfer process competing with internal conversion between singlet states. High QY values were obtained for polymers with isopropylidene or fluorene units in dimethyl sulfoxide (polar solvent), which may be due to the strong overlap of electronic transitions of species from system.

NITROGEN-CONTAINING BIOPOLYMER-BASED CATALYSTS, THEIR PREPARATION AND USES IN HYDROGENATION PROCESSES, REDUCTIVE DEHALOGENATION AND OXIDATION

The present invention relates to a process for the preparation of a nitrogen containing biopolymer-based catalyst by pyrolysis of a metal complex with a nitrogen-containing biopolymer and to the nitrogen containing biopolymer-based catalysts obtainable by this process. In particular, the invention relates to a nitrogen containing biopolymer-based catalyst comprising metal particles and at least one nitrogen containing carbon layer. The invention also relates to the use of a nitrogen containing biopolymer-based catalyst in a hydrogenation process, preferably in a process for hydrogenation of nitroarenes, nitriles or imines; in a reductive dehalogenation process of C-X bonds, wherein X is CI, Br or I, preferably in a process for dehalogenation of organohalides or in a process for deuterium labelling of arenes via dehalogenation of organohalides; or in an oxidation process. Further, the invention relates to a metal complex with the nitrogen containing biopolymer, wherein the metal is a transition metal selected from the group consisting of manganese, ruthenium, cobalt, rhodium, nickel, palladium and platinum, preferably cobalt or nickel, and wherein the nitrogen containing biopolymer is selected from chitosan, chitin and a polyamino acid, preferably chitosan or chitin.

Biomass-Derived Catalysts for Selective Hydrogenation of Nitroarenes

Development of catalytically active materials from biowaste represents an important aspect of sustainable chemical research. Three heterogeneous materials were synthesized from inexpensive biomass-based chitosan and abundant Co(OAc)2 using complexation followed by pyrolysis at various temperatures. These materials were applied in the catalytic hydrogenation of nitroarenes using molecular hydrogen. A variety of diversely functionalized nitroarenes including some pharmaceutically active compounds were converted into aromatic amines in high yields, with high selectivity, and with excellent functional group tolerance. This green protocol has also been implemented for the synthesis of a biologically important TRPC3 inhibitor.

Polytriazole bridged with 2,5-diphenyl-1,3,4-oxadiazole moieties: A highly sensitive and selective fluorescence chemosensor for Ag+

Fluorescent conjugated polytriazoles (FCP 1-4) containing both 2,5-diphenyl-1,3,5-oxadiazole (OXD) and 1,2,3-triazole moieties in the main chain were synthesized from aromatic diazide (1) and dialkynes (2-5) via click polymerization, respectively. In the polymers, OXDs (fluorophores) and triazole rings (generated via CuAAC acting as metal ion ligands) comprise a fluorescent system. The polytriazoles displayed relatively strong emission with quantum yields in the range of 0.20-0.28 at room temperature in DMF. The study on their ion-responsive properties showed that, although all four FCPs have good selectivity for Ag+, the integration of alkoxy side groups (methoxy for FCP 2, hexyloxy for FCP 3 and 2-ethylhexyloxy for FCP 4) to the main chains of the polytriazoles decreased their sensitivity for Ag+via alteration of the polymer aggregation status and electron density of the main chains. Thus FCP 1 is highly sensitive for Ag+, where its Ksv is as high as 1.44 × 105 M-1 and its lowest detection limit is in the ppb range (4.22 × 10-7 M). This study provides an efficient click approach to the synthesis of a novel fluorescence sensor for Ag+ detection, which could expand the application of click polymerization in designing fluorescence sensors based on the triazole unit. This journal is

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.

Nanoscale Fe2O3-based catalysts for selective hydrogenation of nitroarenes to anilines

Production of anilines - key intermediates for the fine chemical, agrochemical, and pharmaceutical industries - relies on precious metal catalysts that selectively hydrogenate aryl nitro groups in the presence of other easily reducible functionalities. Herein, we report convenient and stable iron oxide (Fe2O3) - based catalysts as a more earth-abundant alternative for this transformation. Pyrolysis of iron-phenanthroline complexes on carbon furnishes a unique structure in which the active Fe2O 3 particles are surrounded by a nitrogen-doped carbon layer. Highly selective hydrogenation of numerous structurally diverse nitroarenes (more than 80 examples) proceeded in good to excellent yield under industrially viable conditions.

Copoly(peryleneimide)s containing 1,3,4-oxadiazole rings: Synthesis and properties

New copolyimides containing perylenediimide, oxadiazole and hexafluoroisopropylidene moieties were prepared by one-step polycondensation reaction in solution at high temperature of aromatic diamines containing preformed oxadiazole ring with a mixture of a dianhydride having a perylene ring and another dianhydride with hexafluoroisopropylidene unit. The thermal stability and glass transition temperatures of these copolyimides were measured and compared with those of related polyimides. The solid polymers were also studied by polarized light microscopy and X-ray diffraction which revealed a semicrystalline state consisting of face-to-face arranged columns of perylenediimide units. The film-forming ability and properties of the resulting thin films were investigated by using atom force microscopy and scanning electron microscopy which showed that the films were organized into selfassembled rod-like structures. The UV-Vis and photoluminescence properties in solution and in solid state were also investigated.

Fluorinated heterocyclic polyperyleneimides

New polyperyleneimides containing 1,3,4-oxadiazole rings and hexafluoroisopropylidene linkages were synthesized by solution polycondensation reaction at high temperature of aromatic diamines having oxadiazole rings with a mixture of perylenetetracarboxylic dianhydride and hexafluoroisopropylidene diphthalic dianhydride. The solubility and thermal stability of these polymers were studied and compared with those of related polyimides and polyoxadiazoles. The film-forming ability and the quality of the resulting thin films were investigated by using atom force microscopy and scanning electron microscopy, which showed that the films were organized into self-assembled rod-like structures. The photoluminescence of the polymers, both in solution and in solid state, after irradiation with light of different wavelengths, were also studied.