Trimerization of 4-Amino-3,5-dinitropyrazole: Formation, Preparation, and Characterization of 4-Diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226)

Zhang, Mao‐Xi; Pagoria, Philip F.; Imler, Gregory H.; Parrish, Damon

doi:10.1002/jhet.3434

Title: Trimerization of 4-Amino-3,5-dinitropyrazole: Formation, Preparation, and Characterization of 4-Diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226)

Abstract

4-Amino-3,5-dinitropyrazole (LLM-116, 1) undergoes trimerization to 4-diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226) upon heating. A mechanism is presented and discussed. LLM-226 is a new diazo-based energetic material, thermally stable, and insensitive to impact, friction, and spark. The material may be prepared by heating 1 and 4-diazo-3,5-dinitropyrazole (2) in a mixture of toluene and butyl acetate at 110°C or heating 1 alone in dichlorobenzene at 160°C. The characterization of LLM-226 including X-ray crystallographic analysis and small-scale safety properties will be reported on.

Authors:

^[1]; Pagoria, Philip F. ^[1]; Imler, Gregory H. ^[2]; Parrish, Damon ^[2]

Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Naval Research Lab. (NRL), Washington, DC (United States)

Publication Date:: Tue Jan 29 00:00:00 EST 2019

Research Org.:: Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)

Sponsoring Org.:: USDOE National Nuclear Security Administration (NNSA)

OSTI Identifier:: 1513297

Report Number(s):: LLNL-JRNL-754072
Journal ID: ISSN 0022-152X; 940246

Grant/Contract Number:: AC52-07NA27344

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Heterocyclic Chemistry

Additional Journal Information:: Journal Volume: 56; Journal Issue: 3; Journal ID: ISSN 0022-152X

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Zhang, Mao‐Xi, Pagoria, Philip F., Imler, Gregory H., and Parrish, Damon. Trimerization of 4-Amino-3,5-dinitropyrazole: Formation, Preparation, and Characterization of 4-Diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226).  United States: N. p., 2019. 
Web.  doi:10.1002/jhet.3434.

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                    Zhang, Mao‐Xi, Pagoria, Philip F., Imler, Gregory H., & Parrish, Damon. Trimerization of 4-Amino-3,5-dinitropyrazole: Formation, Preparation, and Characterization of 4-Diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226).  United States.  https://doi.org/10.1002/jhet.3434

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                    Zhang, Mao‐Xi, Pagoria, Philip F., Imler, Gregory H., and Parrish, Damon. Tue .  
"Trimerization of 4-Amino-3,5-dinitropyrazole: Formation, Preparation, and Characterization of 4-Diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226)".  United States.  https://doi.org/10.1002/jhet.3434.  https://www.osti.gov/servlets/purl/1513297.

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@article{osti_1513297,

  title        = {Trimerization of 4-Amino-3,5-dinitropyrazole: Formation, Preparation, and Characterization of 4-Diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226)},

  author       = {Zhang, Mao‐Xi and Pagoria, Philip F. and Imler, Gregory H. and Parrish, Damon},

  abstractNote = {4-Amino-3,5-dinitropyrazole (LLM-116, 1) undergoes trimerization to 4-diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226) upon heating. A mechanism is presented and discussed. LLM-226 is a new diazo-based energetic material, thermally stable, and insensitive to impact, friction, and spark. The material may be prepared by heating 1 and 4-diazo-3,5-dinitropyrazole (2) in a mixture of toluene and butyl acetate at 110°C or heating 1 alone in dichlorobenzene at 160°C. The characterization of LLM-226 including X-ray crystallographic analysis and small-scale safety properties will be reported on.},

  doi          = {10.1002/jhet.3434},

  journal      = {Journal of Heterocyclic Chemistry},

  number       = 3,

  volume       = 56,

  place        = {United States},

  year         = {Tue Jan 29 00:00:00 EST 2019},

  month        = {Tue Jan 29 00:00:00 EST 2019}

}

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Title: Trimerization of 4-Amino-3,5-dinitropyrazole: Formation, Preparation, and Characterization of 4-Diazo-3,5-bis(4-amino-3,5-dinitropyrazol-1-yl) pyrazole (LLM-226)

Abstract

Citation Formats

Synthesis and thermal behaviors of 4-amino-3,5-dinitro-1H-pyrazole journal, November 2012

Efficient Procedure for High-Yield Synthesis of 4-Substituted 3,5-Dinitropyrazoles Using 4-Chloro-3,5-dinitropyrazole journal, June 2012

Four Syntheses of 4-Amino-3,5-dinitropyrazole: Four Syntheses of 4-Amino-3,5-dinitropyrazole journal, April 2014

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Synthesis of polynitrodiazophenols journal, June 1986

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