Synthesis, Crystal Structure and Properties of 2-Azido-6-methyl-5-nitro-pyrimidin-4(3H)-one(AMNP)

被引：0
|
作者：
Hu Y. [1 ]
Yang J.-Q. [1 ]
Zhang J.-G. [1 ]
机构：
[1] State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing
来源：
Zhang, Jian-Guo (zjgbit@bit.edu.cn) | 1600年 / Institute of Chemical Materials, China Academy of Engineering Physics卷 / 28期
关键词：
2-azido-6-methyl-5-nitropyrimidin-4(3H)-one(AMNP); Characterization; Molecular structure; Thermal decomposition;
D O I：
10.11943/CJEM2020006
中图分类号：
学科分类号：
摘要：
To satisfy the growing demand for military and civilian applications, a new energetic compound, 2-azido-6-methyl-5-nitropyrimidin-4(3H)-one(AMNP), was prepared from 5-aminotetrazole and ethyl acetoacetate through a two-step synthesis of cyclization and nitration with a total yield of 60%. Its structure was characterized by element analysis (EA), infrared spectroscopy (IR) and nuclear magnetic resonance (NMR). The single crystal of AMNP was cultured from isopropanol. Its molecular structure and crystal structure were determined by X-ray single crystal diffraction analyzer. The crystal belongs to orthorhombic crystal system, space group Pna21, with Mr=196.14, a=19.800(4) Å, b=5.6660(10) Å, c=14.300(3) Å, V=1604.3(5) Å3, Z=8, Dc=1.624 g•cm-3. The thermal behavior of AMNP was studied by using the differential scanning calorimetry (DSC) and thermo-gravimetric analysis (TG/DTG) method. Its first decomposition peak is 227.39℃ and the second one is 298.75℃, which indicate that it has a good thermal stability. According to standard BAM method, the impact sensitivity is 10 J, and the friction sensitivity is above 360 N. © 2020, Editorial Board of Chinese Journal of Energetic Materials. All right reserved.
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页码：644 / 649
页数：5
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共 24 条
  • [1] WANG Yan-fei, OU Yu-xiang, LIU Jin-quan, Et al., Synthesis of 7-amino-6-nitrobenzodifuroxan, Chemical World, 47, 8, pp. 484-487, (2006)
  • [2] YAN Fan-yong, CHEN Li-gong, YAN Xi-long, Synthesis and applications of rhodamine fluorescent dyes, Progress in Chemistry, 18, 3, pp. 252-254, (2006)
  • [3] Zheng Z, Tran H A, Manivannan S, Et al., Novel nucleoside-based antimalarial compounds, Bioorganic & Medicinal Chemistry Letters, 26, 12, pp. 2861-2865, (2016)
  • [4] Lioux T, Gosselin G, Mathe C., Azido/tetrazole tautomerism in 2-azidoadenine β-D-pentofuranonucleoside Derivatives, European Journal of Organic Chemistry, 24, 20, pp. 3997-4005, (2003)
  • [5] LIU Jin-quan, CHEN Shu-sen, OU Yu-xiang, Synthesis of 2, 6-diamino-3, 5-dinitropyrazing-1-oxide (LLM-105), Chemistry, 6, 2, pp. 151-158, (2006)
  • [6] Lu Lian-ying, WANG Jian-long, CHANG Yong-fang, Et al., New method for synthesis of 7-amino-6-nitro- benzodifuroxan, Chinese Journal of Energetic Materials (Hanneng Cailiao), 14, 6, pp. 436-438, (2006)
  • [7] Kettner M A, Klapoke T M., New energetic polynitro-tetrazoles, Chemistry-A European Journal, 21, 9, pp. 3755-3763, (2015)
  • [8] Wang Y, Liu Y, Song S., Accelerating the discovery of insensitive high energy-density materials by a materials genome approach, Nature Communications, 9, pp. 2444-2452, (2018)
  • [9] Deng M C, Feng Y A, Zhang W Q, Et al., A green metal-free fused-ring initiating substance, Nature Communications, 10, pp. 1339-1347, (2019)
  • [10] Dippold A A, Klapotke T M, Oswald M., Asymmetrically substituted 5, 5'-bistriazoles-nitrogen-rich materials with various energetic functionalities, Dalton Transactions, 42, 31, pp. 11136-11145, (2013)
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