Versatile functionalization of 3,5-diamino-4-nitropyrazole for promising insensitive energetic compounds.

Variation of functional groups offers an efficient approach for tuning properties of materials such as thermal stability, and detonation performance while improving sensitivities to mechanical stimuli. Now versatile functionalization of 3,5-diamino-4-nitropyrazole involving the introduction of a tetrazole ring, or a guanyl group, or ring expansion is described. All of the compounds were fully characterized and some of them (2, 9 and 13) were verified by single crystal X-ray diffraction. Based on their good thermal stabilities and high detonation performance as well as insensitive properties, they are potentially insensitive energetic compounds.

[1]  J. Shreeve,et al.  Green Synthetic Approach for High-Performance Energetic Nitramino Azoles. , 2019, Organic letters.

[2]  Chunlin He,et al.  Aminonitro Groups Surrounding a Fused Pyrazolotriazine Ring: A Superior Thermally Stable and Insensitive Energetic Material , 2019, ACS Applied Energy Materials.

[3]  Yiying Zhang,et al.  Energetic C-trinitromethyl-substituted pyrazoles: synthesis and characterization. , 2019, Dalton transactions.

[4]  Ming Lu,et al.  Recent advances in the syntheses and properties of polynitrogen pentazolate anion cyclo-N5- and its derivatives. , 2018, Chemical Society reviews.

[5]  Chunlin He,et al.  A C-C bonded 5,6-fused bicyclic energetic molecule: exploring an advanced energetic compound with improved performance. , 2018, Chemical communications.

[6]  Ming Lu,et al.  A series of energetic metal pentazolate hydrates , 2017, Nature.

[7]  Wenquan Zhang,et al.  A promising high-energy-density material , 2017, Nature Communications.

[8]  Dheeraj Kumar,et al.  A Highly Stable and Insensitive Fused Triazolo-Triazine Explosive (TTX). , 2017, Chemistry.

[9]  T. Klapötke,et al.  Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes. , 2016, Angewandte Chemie.

[10]  B. Scott,et al.  A high density pyrazolo-triazine explosive (PTX) , 2015 .

[11]  T. Klapötke,et al.  Potassium 1,1'-dinitramino-5,5'-bistetrazolate: a primary explosive with fast detonation and high initiation power. , 2014, Angewandte Chemie.

[12]  Chunlin He,et al.  4-Chloro-3,5-dinitropyrazole: a precursor for promising insensitive energetic compounds , 2013 .

[13]  Yanqiang Zhang,et al.  4-Nitramino-3,5-dinitropyrazole-based energetic salts. , 2012, Chemistry.

[14]  J. Shreeve,et al.  Azole-based energetic salts. , 2011, Chemical reviews.

[15]  C. Roussel,et al.  Selective preparation of 3,4,5-trinitro-1H-pyrazole: a stable all-carbon-nitrated arene. , 2010, Angewandte Chemie.

[16]  C. Ye,et al.  Computational Characterization of Energetic Salts , 2007 .

[17]  J. Guillard,et al.  New synthetic route to diaminonitropyrazoles as precursors of energetic materials , 2003 .

[18]  V. Makarov,et al.  Highly polarized enamines. , 1997 .

[19]  D. Wales,et al.  Empirical Correlations between Thermodynamic Properties and Intermolecular Forces , 1995 .

[20]  M. S. Pevzner,et al.  Diazotization of aminonitropyrazoles , 1976 .