A C-C bonded 5,6-fused bicyclic energetic molecule: Exploring an advanced energetic compound with improved performance

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

doi:10.1039/c8cc05987j

A C-C bonded 5,6-fused bicyclic energetic molecule: Exploring an advanced energetic compound with improved performance

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

^*Corresponding author for this work

University of Idaho
Naval Research Laboratory

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

74 Citations (Scopus)

Abstract

A C-C bonded amino-nitro pyrazole (7) and its ring-expansion product (9) have been synthesized and characterized. The synthetic route to 9 proceeds in several steps from the commercial substrate diethyl oxalate and acetone. The process was found to be straightforward, practical and easily scalable. Both of these structures were confirmed by single crystal X-ray diffraction. Compound 9 with a high density (1.85 g cm^-3) at room temperature, excellent thermal stability (T_d: 315 °C), good detonation performance and low sensitivity to impact and friction has potential as a high-temperature energetic material.

Original language	English
Pages (from-to)	10566-10569
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	75
DOIs	https://doi.org/10.1039/c8cc05987j
Publication status	Published - 2018
Externally published	Yes

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title = "A C-C bonded 5,6-fused bicyclic energetic molecule: Exploring an advanced energetic compound with improved performance",

abstract = "A C-C bonded amino-nitro pyrazole (7) and its ring-expansion product (9) have been synthesized and characterized. The synthetic route to 9 proceeds in several steps from the commercial substrate diethyl oxalate and acetone. The process was found to be straightforward, practical and easily scalable. Both of these structures were confirmed by single crystal X-ray diffraction. Compound 9 with a high density (1.85 g cm-3) at room temperature, excellent thermal stability (Td: 315 °C), good detonation performance and low sensitivity to impact and friction has potential as a high-temperature energetic material.",

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

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc05987j",

language = "English",

volume = "54",

pages = "10566--10569",

journal = "Chemical Communications",

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T1 - A C-C bonded 5,6-fused bicyclic energetic molecule

T2 - Exploring an advanced energetic compound with improved performance

AU - Tang, Yongxing

AU - He, Chunlin

AU - Imler, Gregory H.

AU - Parrish, Damon A.

AU - Shreeve, Jean'Ne M.

PY - 2018

Y1 - 2018

N2 - A C-C bonded amino-nitro pyrazole (7) and its ring-expansion product (9) have been synthesized and characterized. The synthetic route to 9 proceeds in several steps from the commercial substrate diethyl oxalate and acetone. The process was found to be straightforward, practical and easily scalable. Both of these structures were confirmed by single crystal X-ray diffraction. Compound 9 with a high density (1.85 g cm-3) at room temperature, excellent thermal stability (Td: 315 °C), good detonation performance and low sensitivity to impact and friction has potential as a high-temperature energetic material.

AB - A C-C bonded amino-nitro pyrazole (7) and its ring-expansion product (9) have been synthesized and characterized. The synthetic route to 9 proceeds in several steps from the commercial substrate diethyl oxalate and acetone. The process was found to be straightforward, practical and easily scalable. Both of these structures were confirmed by single crystal X-ray diffraction. Compound 9 with a high density (1.85 g cm-3) at room temperature, excellent thermal stability (Td: 315 °C), good detonation performance and low sensitivity to impact and friction has potential as a high-temperature energetic material.

UR - https://www.scopus.com/pages/publications/85053537234

U2 - 10.1039/c8cc05987j

DO - 10.1039/c8cc05987j

M3 - Article

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AN - SCOPUS:85053537234

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SP - 10566

EP - 10569

JO - Chemical Communications

JF - Chemical Communications

IS - 75

ER -

A C-C bonded 5,6-fused bicyclic energetic molecule: Exploring an advanced energetic compound with improved performance

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