Aminonitro Groups Surrounding a Fused Pyrazolotriazine Ring: A Superior Thermally Stable and Insensitive Energetic Material

Yongxing Tang; Chunlin He; Gregory H. Imler; Damon A. Parrish; Jean'Ne M. Shreeve

doi:10.1021/acsaem.9b00049

Aminonitro Groups Surrounding a Fused Pyrazolotriazine Ring: A Superior Thermally Stable and Insensitive Energetic Material

Yongxing Tang, Chunlin He, Gregory H. Imler, Damon A. Parrish, Jean'Ne M. Shreeve^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

162 Citations (Scopus)

Abstract

Nitrogen-rich heterocyclic compounds offer promising potential backbones for constructing various high energy density compounds. Selective diazotization of 3,5-diamino-4-nitropyrazole (1) with tert-butyl nitrite followed by treatment with the sodium salt of nitroacetonitrile gives rise to a fused pyrazolotriazine ring (5) surrounded by amino and nitro groups. Compound 5, confirmed by single-crystal X-ray diffraction, has a remarkable thermal decomposition temperature of 355 °C, a high density of 1.90 g cm^-3, and low impact and friction sensitivities. The detonation performance is also superior to TATB. These advantages make 5 a promising candidate as a heat-resistant explosive.

Original language	English
Pages (from-to)	2263-2267
Number of pages	5
Journal	ACS Applied Energy Materials
Volume	2
Issue number	3
DOIs	https://doi.org/10.1021/acsaem.9b00049
Publication status	Published - 25 Mar 2019
Externally published	Yes

Keywords

energetic compound
fused compound
heat-resistant explosive
pyrazole
triazine

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10.1021/acsaem.9b00049

Cite this

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title = "Aminonitro Groups Surrounding a Fused Pyrazolotriazine Ring: A Superior Thermally Stable and Insensitive Energetic Material",

abstract = "Nitrogen-rich heterocyclic compounds offer promising potential backbones for constructing various high energy density compounds. Selective diazotization of 3,5-diamino-4-nitropyrazole (1) with tert-butyl nitrite followed by treatment with the sodium salt of nitroacetonitrile gives rise to a fused pyrazolotriazine ring (5) surrounded by amino and nitro groups. Compound 5, confirmed by single-crystal X-ray diffraction, has a remarkable thermal decomposition temperature of 355 °C, a high density of 1.90 g cm-3, and low impact and friction sensitivities. The detonation performance is also superior to TATB. These advantages make 5 a promising candidate as a heat-resistant explosive.",

keywords = "energetic compound, fused compound, heat-resistant explosive, pyrazole, triazine",

author = "Yongxing Tang and Chunlin He and Imler, \{Gregory H.\} and Parrish, \{Damon A.\} and Shreeve, \{Jean'Ne M.\}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = mar,

day = "25",

doi = "10.1021/acsaem.9b00049",

language = "English",

volume = "2",

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T1 - Aminonitro Groups Surrounding a Fused Pyrazolotriazine Ring

T2 - A Superior Thermally Stable and Insensitive Energetic Material

AU - Tang, Yongxing

AU - He, Chunlin

AU - Imler, Gregory H.

AU - Parrish, Damon A.

AU - Shreeve, Jean'Ne M.

PY - 2019/3/25

Y1 - 2019/3/25

N2 - Nitrogen-rich heterocyclic compounds offer promising potential backbones for constructing various high energy density compounds. Selective diazotization of 3,5-diamino-4-nitropyrazole (1) with tert-butyl nitrite followed by treatment with the sodium salt of nitroacetonitrile gives rise to a fused pyrazolotriazine ring (5) surrounded by amino and nitro groups. Compound 5, confirmed by single-crystal X-ray diffraction, has a remarkable thermal decomposition temperature of 355 °C, a high density of 1.90 g cm-3, and low impact and friction sensitivities. The detonation performance is also superior to TATB. These advantages make 5 a promising candidate as a heat-resistant explosive.

AB - Nitrogen-rich heterocyclic compounds offer promising potential backbones for constructing various high energy density compounds. Selective diazotization of 3,5-diamino-4-nitropyrazole (1) with tert-butyl nitrite followed by treatment with the sodium salt of nitroacetonitrile gives rise to a fused pyrazolotriazine ring (5) surrounded by amino and nitro groups. Compound 5, confirmed by single-crystal X-ray diffraction, has a remarkable thermal decomposition temperature of 355 °C, a high density of 1.90 g cm-3, and low impact and friction sensitivities. The detonation performance is also superior to TATB. These advantages make 5 a promising candidate as a heat-resistant explosive.

KW - energetic compound

KW - fused compound

KW - heat-resistant explosive

KW - pyrazole

KW - triazine

UR - https://www.scopus.com/pages/publications/85064820914

U2 - 10.1021/acsaem.9b00049

DO - 10.1021/acsaem.9b00049

M3 - Article

AN - SCOPUS:85064820914

SN - 2574-0962

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JO - ACS Applied Energy Materials

JF - ACS Applied Energy Materials

IS - 3

ER -

Aminonitro Groups Surrounding a Fused Pyrazolotriazine Ring: A Superior Thermally Stable and Insensitive Energetic Material

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Keywords

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