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Title: Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials

Journal Article · · Chemistry of Heterocyclic Compounds
 [1];  [1];  [1];  [1];  [2]
  1. Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
  2. Naval Research Lab. (NRL), Washington, DC (United States)
+ Show Author Affiliations

Synthesis and characterization of several multicyclic oxadiazoles, 3,5-bis(4-nitrofurazan-3-yl)-1,2,4-oxadiazole, 3,3'-bis(4-nitrofurazan-3-yl)-5,5'-bi(1,2,4-oxadiazole), 3-(4-nitrofurazan-3-yl)-1,2,4-oxadiazol-5-amine, and salts of 1-hydroxytetrazoles, ammonium 5,5'-(1,2,4-oxadiazole-3,5-diyl)bis(1H-tetrazol-1-olate) and hydroxylammonium 5,5'-{[3,3'-bi(1,2,4-oxadiazole)]-5,5'-diyl}bis(1H-tetrazol-1-olate), as energetic materials are reported here. Two of the compounds, 3,5-bis(4-nitrofurazan-3-yl)-1,2,4-oxadiazole and 3,3'-bis(4-nitrofurazan-3-yl)-5,5'-bi(1,2,4-oxadiazole), have attractive single crystal densities of 1.91 and 1.94 g·cm–3 (at 20°C), respectively. The design of these materials has been based on the idea that these multicyclic compounds with a 1,2,4-oxadiazole core will have good thermal stability and high density because of their 3,5-substitution pattern and the possibility of achieving a planar conformation. The various synthetic approaches and interesting chemistry observed during the construction of these new heterocycles has been described.

Research Organization:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States); Naval Research Lab. (NRL), Washington, DC (United States)
Sponsoring Organization:
USDOE National Nuclear Security Administration (NNSA); USDOD
Grant/Contract Number:
AC52-07NA27344
OSTI ID:
1524284
Report Number(s):
LLNL-JRNL-720247; 865679
Journal Information:
Chemistry of Heterocyclic Compounds, Vol. 53, Issue 6-7; ISSN 0009-3122
Publisher:
SpringerCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 51 works
Citation information provided by
Web of Science

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Cited By (15)

Pyrazole-Tetrazole Hybrid with Trinitromethyl, Fluorodinitromethyl, or (Difluoroamino)dinitromethyl Groups: High-Performance Energetic Materials journal April 2018
Synthesis and Characterization of 3‐(5‐(Fluorodinitromethyl)‐1 H ‐1,2,4‐triazol‐3‐yl)‐4‐nitrofurazan: A Novel Promising Energetic Component of Boron‐based Fuels for Rocket Ramjet Engines journal October 2019
Incorporating Energetic Moieties into Four Oxadiazole Ring Systems for the Generation of High-Performance Energetic Materials journal May 2018
1,2,4‐Oxadiazole‐Bridged Polynitropyrazole Energetic Materials with Enhanced Thermal Stability and Low Sensitivity journal October 2019
1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance journal November 2019
Synthesis and some transformations of 2-[(4-aminofurazan-3-yl)-1H-1,2,4-triazol-5-yl]acetic acid derivatives journal November 2018
Synthesis and structural features of 2-halo-2,2-dinitroacetamidoximes journal November 2018
Synthesis and characterization of furazan derivatives and their evaluation as antitumor agents journal June 2019
Nitramino-functionalized tetracyclic oxadiazoles as energetic materials with high performance and high stability: crystal structures and energetic properties journal January 2018
Azasydnone – novel “green” building block for designing high energetic compounds journal January 2018
1,2,4-Oxadiazole-derived polynitro energetic compounds with sensitivity reduced by a methylene bridge journal January 2019
Aminonitrones as highly reactive bifunctional synthons. An expedient one-pot route to 5-amino-1,2,4-triazoles and 5-amino-1,2,4-oxadiazoles – potential antimicrobials targeting multi-drug resistant bacteria journal January 2019
A novel energetic framework combining the advantages of furazan and triazole: a design for high-performance insensitive explosives journal January 2020
Novel energetic metal–organic frameworks assembled from the energetic combination of furazan and tetrazole journal January 2020
Effect of counter-ion on packing and crystal density of 5,5′-(3,3′-bi[1,2,4-oxadiazole]-5,5′-diyl)bis(1 H -tetrazol-1-olate) with five different cations journal March 2018

Linked Research (5)

Figures / Tables (20)

Scheme 1(p. 3)figure Scheme 1
Scheme 2(p. 4)figure Scheme 2
Scheme 3(p. 4)figure Scheme 3
Scheme 4(p. 5)figure Scheme 4
Scheme 5(p. 5)figure Scheme 5
Scheme 6(p. 6)figure Scheme 6
Table 1(p. 6)table Table 1
Scheme 7(p. 7)figure Scheme 7
Table 2(p. 7)table Table 2
Figure 1(p. 8)figure Figure 1
Scheme 8(p. 8)figure Scheme 8
Table 3(p. 8)table Table 3
Figure 2(p. 9)figure Figure 2
Scheme 9(p. 9)figure Scheme 9
Figure 3(p. 10)figure Figure 3
Scheme 10(p. 10)figure Scheme 10
Scheme 11(p. 11)figure Scheme 11
Figure 4(p. 12)figure Figure 4
Figure 5(p. 13)figure Figure 5
Scheme 12(p. 13)figure Scheme 12

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
furazans
1-hydroxytetrazoles
nitroheterocycles
1
2
4-oxadiazoles
tetrazoles
energetic materials