Nitrotriazolone
Chemical compound
From Wikipedia, the free encyclopedia
Nitrotriazolone (NTO) is a cyclic semicarbazide-derived high explosive first identified in 1905, but not thoroughly researched until the 1980s.[2] NTO is currently being used by the US Army in specialty insensitive munitions.[3]
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| Names | |
|---|---|
| Preferred IUPAC name
5-nitro-1,2-dihydro-3H-1,2,4-triazol-3-one | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | NTO |
| ChemSpider | |
| ECHA InfoCard | 100.012.050 |
| EC Number |
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| MeSH | C420648 |
PubChem CID |
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| UNII | |
| UN number | 0490 |
CompTox Dashboard (EPA) |
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| Properties | |
| C2H2N4O3 | |
| Molar mass | 130.063 g·molâ1 |
| Appearance | Off white, yellowish beige color to light yellow powder, crystals, or prills |
| Odor | Odourless |
| Density | 1.9 g/cm3 (20 °C) |
| Melting point | 268â271 °C (514â520 °F; 541â544 K) |
| 17,200 mg/L | |
| Solubility | Soluble in acetone, ethyl acetate Slightly soluble in dichloromethane |
| log P | â1.699 (22 °C) |
| Acidity (pKa) | 3.76 (20 °C) |
| Explosive data | |
| Shock sensitivity | Very low |
| Friction sensitivity | Very low |
| Detonation velocity | 8,500 m/s |
| Thermochemistry | |
Heat capacity (C) |
124.5 J/K at (47 °C) |
Std enthalpy of combustion (ÎcH⦵298) |
â934.4 kJ/mol |
| Hazards | |
| GHS labelling: | |
    | |
| Danger | |
| H209, H223, H242, H301, H313, H315, H319, H333, H335 | |
| P210, P220, P260, P262, P270, P280 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Nitrotriazolone is getting progressively adopted in novel explosive formulations, such as IMX-101, a new, safer alternative to TNT specially devised in 2010 by BAE Systems, where it is combined with 2,4-dinitroanisole (DNAN) and nitroguanidine. As such, NTO is found in the vast majority of IMX formulations. The Picatinny Arsenal has also adopted the implementation of NTO and DNAN in many of their likewise newly developed insensitive explosive mixtures, which share many of the same applications of the IMXs. [4]
Properties
Nitrotriazolone shows ketoâenol tautomerism through proton transfer reactions. The keto form shows significantly different stability to heat, friction, and impact.[5]
Nitrotriazolone can form either a mono- or dihydrate.[5]
Preparation
NTO was first made in 1905[6] in a two step process. Semicarbazide hydrochloride is condensed with formic acid to produce 1,2,4-triazol-3-one, which is nitrated with nitric acid to form nitrotriazolone.[7][5]
Toxicity
In vivo studies showed the nitrotriazolone is absorbed through the skin and gastrointestinal tract. In the kidneys, NTO is broken down into 5-amino-1,2,4-triazol-3-one, which undergoes oxidative denitrification and forms urazoles and nitrites in rats.[8]