Synthesis of N-amino- and N-nitramino-nitroimidazoles

Duddu, Raja; Dave, Paritosh R.; Damavarapu, Reddy; Gelber, Nathan; Parrish, Damon A.

doi:10.1016/j.tetlet.2009.11.046

Cited by 36 publications

(17 citation statements)

References 14 publications

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“…4,5-DNI,ayellow solid with am .p. 188-9 8C, was extracted from the reaction mixture with CHCl 3 [73].T he synthesis of 1-amino-2,4-dinitroimidazole( ADNI)w as reported by Duddu and co-workers [75] by allowing 2,4-DNI to react with O-mesitylenesulfonylhydroxylamine( MSH)t og ive ADNI in 45 %y ield.A DNI has ad ensity of 1.75 gcm À3 ,s imi-lar to 2,4-DNI and aD SC peak exothermo f1 72 8C. The sensitivity of this compound was not reported.…”

Section: Small-ring Heterocyclic Insensitive Energetic Compoundsmentioning

confidence: 99%

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

Pagoria

2016

Propellants Explo Pyrotec

104

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1IntroductionIn general, highe xplosivesa re categorized as primary,s econdary,a nd tertiary explosives, basedo nt heir sensitivity to mechanical insults. Primarye xplosivesa re very sensitive to mechanical and electricali nitiation and are used as initiating explosives in an explosivet rain. Secondary explosives are less sensitivet om echanical stimuli, although in many cases can still be somewhat sensitive materials. Te rtiary explosives are generallyv ery insensitivee xplosivesv ery often consistingo fa no xidizer and af uel, and are generallyu sed in mining. Subsets of secondary explosives are insensitive energetic compoundso rm aterials. Insensitive energetic compounds are defined as compoundst hat have relatively benign responses to externali nsults such as impact, shock, spark, friction, and heat. Understandingt he various factors that affectt he sensitivity of energetic compoundst ov arious mechanical insults plays an important role in the design of new,i nsensitive, and thermally stable higher-performance energetic materials. While there have been several excellent reviewsa nd books on new energetic compounds in the past 15 years [1-7],t his review will concentrate on insensitivee nergetic compounds. Also this paper will concentrate on insensitive energeticc ompounds and not discuss insensitivee nergetic formulationso rm ixtures or engineering methods to decrease sensitivity.Althoughs park and friction sensitivity are important, impact, shock, and thermal stabilitya re the most commonly used measurements to determine the relatives ensitivity of ag iven compoundc ompared to knowns tandards. In this paper the term insensitivity will refer mainly to impact and thermal sensitivity.I mpact sensitivity is generally measured by using a" drop hammer" impact machine, in which an anvil of ag iven weight (generally 5kg) is allowed to impact as mall sample (ca. 35 mg) of an explosive and the responsei sr ecorded. Historically,d rop hammer results (Dh 50 or H 50 )w ere reported as the height, at which there is a5 0% probabilityo fi gnition. In recenty ears, some authors are convertingt he recorded drop hammer heights to Joules and are reporting the energy required at which there is a5 0% probability of ignition. Thermal stabilitym ay be measured using several methods including differential scanning calorimetry (DSC), differential thermala nalysis (DTA), chemical reactivity test (CRT), vacuum stability test (VTS), slow cook-off test, and fast cook-off test.The industry standardf or an insensitive energetic compound is 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), ar easonably powerful explosive, whose response to shock, thermal, impact and friction insultsi ss ignificantly more benign than that of any other knownm aterial of comparable energy [8,9].T his "enhanced" insensitivity of TATB has led to as ignificant amount of studies on how various physical properties including molecular structure,c rystal structure, and crystal packing of TATB contributes to its "enhanced" insensitivity,a nd how these physical properties c...

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Section: Small-ring Heterocyclic Insensitive Energetic Compoundsmentioning

confidence: 99%

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

Pagoria

2016

Propellants Explo Pyrotec

104

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“…[1][2][3][4] It has been reported in the literature that imidazole derivatives with two or more than two nitro groups have been predicted to be highly powerful, but insensitive explosives. [1][2][3][4] It has been reported in the literature that imidazole derivatives with two or more than two nitro groups have been predicted to be highly powerful, but insensitive explosives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, single crystal structure and performance of N-substituted derivatives of dinitroimidazole

Hou

Liu

2013

New J. Chem.

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The N-substituted derivatives of dinitroimidazoles have been synthesized for application as energetic materials. The synthesized compounds were fully characterized by 1 H 13 C NMR spectroscopy and elemental analysis. Most of them were determined by single crystal X-ray diffraction. The calculated densities of the compounds range between 1.89 and 1.91 g cm À3 and the experimental densities between 1.75 and 1.84 g cm À3 , as obtained by X-ray crystallographic analysis. Notably, densities of the N-substituted derivatives of dinitroimidazoles are increased when two amino groups are introduced but decreased when one amino group is introduced.

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“…We first synthesized N‐amine‐2,4‐dinitroimidazole from 2,4‐dinitroimidazole in two steps following an established literature protocol ,. (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

The Preparation and Properties of Submicrometer‐Sized N‐Amino‐2,4‐dinitroimidazole (ADNI): A Novel and Promising Initiating Explosive for Applications in Short Pulse Initiation Slapper Detonators

Wang

et al. 2018

ChemistrySelect

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We describe for the first time a spray‐recrystallization method to prepare sub‐micrometer N‐amino‐2,4‐dinitroimidazole (ADNI) and test its critical diameters below 3 mm. The uniform sub‐micrometer ADNI has better sensitivity to short impulse shock waves with the 50% and 99.9% initiation currents at 2.45 kA and 2.67 kA, respectively, which is much better than sub‐micrometer LLM‐105 (3.11 kA and 3.46 kA, respectively) and DAAF (3.7 kA and 4.75 kA, respectively). The detonation velocity for ADNI (7.8 km⋅s−1 at a density of 1.67 g⋅cm−3) is greater than that of LLM‐105 (7.54 km⋅s−1 at the density of 1.63 g⋅cm−3) and haxanitrostilbene (HNS) (6.8 km⋅s−1). ADNI also has a higher decomposition temperature (Td =265.8 °C) and a better thermal stability (5S shotpoint of 312 °C) with low impact, friction, and electric spark sensitivities (>40 N, >360 N, and 2.20 J). These metrics are comparable to LLM‐105 (0–30 N, >360 N, and 1.02 J) and HNS (26 N, 240 N, and 1.77 J). The high stability and good detonation properties of sub‐micrometer ADNI clearly shows that it is insensitive to impact stimulus and long pulse stimulation, while also being sensitive to short impulse shock waves. This suggests that it is a promising initiating explosive for slapper detonators.

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Synthesis of N-amino- and N-nitramino-nitroimidazoles

Cited by 36 publications

References 14 publications

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

Synthesis, single crystal structure and performance of N-substituted derivatives of dinitroimidazole

The Preparation and Properties of Submicrometer‐Sized N‐Amino‐2,4‐dinitroimidazole (ADNI): A Novel and Promising Initiating Explosive for Applications in Short Pulse Initiation Slapper Detonators

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