An optimized synthesis of 2,5-bis(4-aminophenyl)-1,3,4-oxadiazole

PDF(906 KB)

Journal of Beijing University of Chemical Technology ›› 2012, Vol. 39 ›› Issue (1) : 17-19.

化学与化学工程

ZHANG Chen;HAO HaiJun;WAN PingYu

Author information +

History +

Abstract

An optimized two-step synthesis of 2,5-bis(4-aminophenyl)-1,3,4-oxadiazole has been established. The reaction of 4-nitrobenzoic acid and semicarbazide hydrochloride at 150-160℃ for 2h, using polyphosphoric acid as the dehydrating reagent, afforded 2,5-bis(4-nitrophenyl)-1,3,4-oxadiazole in 89% yield. This was subsequently reduced with Na2S in DMF at 100℃ for 4h, to give the title compound in 85% yield. The as-prepared title compound is sufficiently pure for further uses.

Cite this article

EndNote

Ris (Procite)

Bibtex

Download Citations

ZHANG Chen;HAO HaiJun;WAN PingYu. An optimized synthesis of 2,5-bis(4-aminophenyl)-1,3,4-oxadiazole[J]. Journal of Beijing University of Chemical Technology, 2012, 39(1): 17-19

References

[1］TakadaN, Tsutsui T, Saito S. Control of emission characteristics in organic thin film electroluminescent diodes using an optical-microcavity structure[J]. Applied Physics Letters, 1993, 63(15): 2032-2034. 
[2] KidoJ, Hayase H, Hongawa K, et al. Bright red light-emitting organic electroluminescent devices having a europium complex as an emitter[J]. Applied Physics Letters, 1994, 65(17): 2124-2126. 
[3] EraM, Morimoto S, Tsutsui T, et al. Organic-inorganic heterostructure electroluminescent devices using a layered perovskite semiconductor (C6H5C2H4NH3)2PbI4[J]. Applied Physics Letters, 1994, 65(6): 676-678. 
[4] Kawamoto M, Mochizuki H, Ikeda T, et al. Charge carrier transport properties in polymer liquid crystals containing oxadiazole and amine moieties in the same side chain[J]. The Journal of Physical Chemistry B, 2005, 109(19): 9226-9230. 
[5] Zhang X B, Tang B C, Zhang P, et al. Synthesis and characterization of 1,3,4-oxadiazole derivatives containing alkoxy chains with different lengths [J]. Journal of Molecular Structure, 2007, 846: 55-64. 
[6] 张玉祥, 刘波, 高仁孝, 等. 蓝色有机电致发光材料OXD-7的合成及性能[J]. 发光学报, 2006, 27(4): 557-560. 
Zhang Y X, Liu B, Gao R X, et al. Synthesis and properties of a blue organic electroluminescent material[J]. Chinese Journal of Luminescence, 2006, 27(4): 557-560. （in Chinese）
[7] 柴春鹏, 范星河, 陈小芳, 等. 含1,3,4-噁二唑环聚合物电致发光材料的近期进展[J]. 化学进展, 2006, 18(11): 1498-1507. 
Cai C P, Fan X H, Chen X F, et al. Polymer electroluminescent materials with 1,3,4-oxadiazole[J]. Progress in Chemistry, 2006, 18(11): 1498-1507. （in Chinese）
[8] 潘家杏, 张遂坡, 高振衡. 2,5-二芳基噁二唑衍生物的合成及光性能的研究[J]. 高等学校化学学报, 1987, 8(2): 137-140. 
Pan J X, Zhang S B, Gao Z H. Synthesis and optical performance of 2,5-diaryl oxadiazoles [J]. Chemical Journal of Chinese Universities, 1987, 8(2): 137-140. （in Chinese）
[9] Siegrist A E, Maeder E, Dünnenberger M, et al. Verfahren zur Herstellung von 1,3,4-Oxadiazolen: Swiss, 383985[P]. 1965-01-29.
[10] Davis M C, Chafin A P. A convenient method for the preparation of 2,5-bis(4-aminophenyl)-1,3,4oxadiazole[J]. Organic Preparations and Procedures International, 2004, 36(4): 375-379.

PDF(906 KB)

2595

Accesses

Citation

Detail

Sections

Recommended

Abstract
Cite this article
References

Received	Revised	Published
2011-05-06	1900-01-01	2012-01-20
Issue Date
2012-01-20

Please choose a citation manager

Content to export

Abstract

Cite this article

{{custom_sec.title}}

{{custom_sec.title}}

References

{{custom_fnGroup.title_en}}

Footnotes

模态框（Modal）标题

Please choose a citation manager

Content to export

Abstract

Cite this article

{{custom_sec.title}}

{{custom_sec.title}}

References

{{custom_fnGroup.title_en}}

Footnotes