Names | |
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Preferred IUPAC name 5-Nitro-1,2-dihydro-3H-1,2,4-triazin-3-one | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | NTO |
ChemSpider | |
ECHA InfoCard | 100.012.050 |
EC Number |
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MeSH | C420648 |
PubChem CID | |
UNII | |
UN number | 0490 |
CompTox Dashboard (EPA) | |
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Properties | |
C2H2N4O3 | |
Molar mass | 130.063 g·mol−1 |
Appearance | Off white, yellowish beige color to light yellow powder, crystals, or prills |
Odor | Odourless |
Density | 1.9 g/cm3 (20 °C) |
Melting point | 268–271 °C (514–520 °F; 541–544 K) |
17,200 mg/L | |
Solubility | Soluble in acetone, ethyl acetate Slightly soluble in dichloromethane |
log P | -1.699 (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 (ΔcH⦵298) | -934.4 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). |
Nitrotriazolone (NTO) is a heterocyclic ketone high explosive first identified in 1905, but research into its explosive properties was not conducted until the 1980s. [2] NTO is currently being used by the US Army in munitions, specifically Insensitive munitions replacing those made with legacy explosives. [3]
Nitrotriazolone is being progressively made use of 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 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]
Nitrotriazolone shows keto–enol tautomerism through proton transfer reactions. The keto form shows significantly different stability to heat, friction, and impact. [5]
Nitrotriazolone can form either mono or a di hydrate. [5]
NTO was first made in 1905 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. [6] [5]
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. [7]
RDX (abbreviation of "Research Department eXplosive") or hexogen, among other names, is an organic compound with the formula (O2N2CH2)3. It is white, odorless and tasteless, widely used as an explosive. Chemically, it is classified as a nitroamine alongside HMX, which is a more energetic explosive than TNT. It was used widely in World War II and remains common in military applications.
An explosive is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An explosive charge is a measured quantity of explosive material, which may either be composed solely of one ingredient or be a mixture containing at least two substances.
Nitroglycerin (NG), also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Discovered in 1847 by Ascanio Sobrero, nitroglycerin has been used as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. It is combined with nitrocellulose to form double-based smokeless powder, which has been used as a propellant in artillery and firearms since the 1880s.
Trinitrotoluene, more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard comparative convention of bombs and asteroid impacts. In chemistry, TNT is used to generate charge transfer salts.
Cordite is a family of smokeless propellants developed and produced in Britain since 1889 to replace black powder as a military firearm propellant. Like modern gunpowder, cordite is classified as a low explosive because of its slow burning rates and consequently low brisance. These produce a subsonic deflagration wave rather than the supersonic detonation wave produced by brisants, or high explosives. The hot gases produced by burning gunpowder or cordite generate sufficient pressure to propel a bullet or shell to its target, but not so quickly as to routinely destroy the barrel of the gun.
C-4 or Composition C-4 is a common variety of the plastic explosive family known as Composition C, which uses RDX as its explosive agent. C-4 is composed of explosives, plastic binder, plasticizer to make it malleable, and usually a marker or odorizing taggant chemical. C-4 has a texture similar to modelling clay and can be molded into any desired shape. C-4 is relatively insensitive and can be detonated only by the shock wave from a detonator or blasting cap.
Dinitrogen tetroxide, commonly referred to as nitrogen tetroxide (NTO), and occasionally (usually among ex-USSR/Russia rocket engineers) as amyl, is the chemical compound N2O4. It is a useful reagent in chemical synthesis. It forms an equilibrium mixture with nitrogen dioxide. Its molar mass is 92.011 g/mol.
SS Richard Montgomery was an American Liberty cargo ship built during World War II. She was named after Richard Montgomery, an Irish officer who fought in the American Revolutionary War.
Amatol is a highly explosive material made from a mixture of TNT and ammonium nitrate. The British name originates from the words ammonium and toluene. Similar mixtures were known as Schneiderite in France. Amatol was used extensively during World War I and World War II, typically as an explosive in military weapons such as aircraft bombs, shells, depth charges, and naval mines. It was eventually replaced with alternative explosives such as Composition B, Torpex, and Tritonal.
Insensitive munitions are munitions that are designed to withstand stimuli representative of severe but credible accidents. The current range of stimuli are shock, heat and adjacent detonating munitions. A munition can have its vulnerability reduced by a number of means used on their own or in combination such as a reduced vulnerability energetic material, design features, additions or changes to packaging etc. The munition must still retain its terminal effect and performance within acceptable parameters.
White phosphorus munitions are weapons that use one of the common allotropes of the chemical element phosphorus. White phosphorus is used in smoke, illumination, and incendiary munitions, and is commonly the burning element of tracer ammunition. Other common names for white phosphorus munitions include WP and the slang terms Willie Pete and Willie Peter, which are derived from William Peter, the World War II phonetic alphabet rendering of the letters WP. White phosphorus is pyrophoric ; burns fiercely; and can ignite cloth, fuel, ammunition, and other combustibles.
FOX-7 or 1,1-diamino-2,2-dinitroethylene(DADNE) is an insensitive high explosive compound. It was first synthesized in 1998 by the Swedish National Defence Research Institute (FOS). The name FOX-7 is derived from the acronym of the Swedish Defence Research Agency (FOI), with the I replaced by an X to indicate an explosive, as in RDX and HMX.
Nitroguanidine - sometimes abbreviated NGu - is a colorless, crystalline solid that melts at 257 °C and decomposes at 254 °C. Nitroguanidine is an extremely insensitive but powerful high explosive. Wetting it with > 20 wt.-% water effects desensitization from HD 1.1 down to HD 4.1 . Nitroguanidine is used as an energetic material, i.e., propellant or high explosive, precursor for insecticides, and for other purposes.
Avobenzone is an oil-soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays.
Deferasirox, sold under the brand name Exjade & Asunra & Oleptiss both by Novartis among others, is an oral iron chelator. Its main use is to reduce chronic iron overload in patients who are receiving long-term blood transfusions for conditions such as beta-thalassemia and other chronic anemias. It is the first oral medication approved in the United States for this purpose.
The triazol-5-ylidenes are a group of persistent carbenes which includes the 1,2,4-triazol-5-ylidene system and the 1,2,3-triazol-5-ylidene system. As opposed to the now ubiquitous NHC systems based on imidazole rings, these carbenes are structured from triazole rings. 1,2,4-triazol-5-ylidene can be thought of as an analog member of the NHC family, with an extra nitrogen in the ring, while 1,2,3-triazol-5-ylidene is better thought of as a mesoionic carbene (MIC). Both isomers of this group of carbenes benefit from enhanced stability, with certain examples exhibiting greater thermal stability, and others extended shelf life.
A sympathetic detonation, also called flash over or secondary/secondaries (explosion), is a detonation, usually unintended, of an explosive charge by a nearby explosion.
IMX-101 is a high-performance insensitive high explosive composite mixture developed by BAE Systems and the United States Army to replace TNT in artillery shells. IMX stands for "Insensitive Munitions eXplosives", which refers to the purpose of IMX-101: to provide explosive force equivalent to TNT without its sensitivity to shocks such as gunfire, explosions from improvised explosive devices, fire, and shrapnel. For example, it is believed that a training incident in Nevada which killed seven Marines would not have occurred with the new explosive. On March 23, 2013, the United States Army ordered $780 million worth of the explosive, with a production of millions of pounds annually, to be produced by BAE at Holston Army Ammunition Plant in Tennessee. The new explosive will cost $8 per pound, compared to $6 per pound for TNT. As of 2023, IMX-101 filled shells are being used in the 2022 Russian invasion of Ukraine.
2,4-Dinitroanisole (DNAN) is a low sensitivity organic compound. It has an anisole (methoxybenzene) core, with two nitro groups (–NO2) attached.
TEX is a dense nitramine high explosive, that derives from the very powerful and sensitive high explosive CL-20. Though related to CL-20 in that is shares the same cage structure, TEX is more easily synthesized in good yield from inexpensive starting materials. Unlike CL-20, TEX is friction insensitive, bears a low impact sensitivity, and possesses a very low shock sensitivity and large critical diameter, making it an interesting explosive filler for insensitive munitions. Its systematic name, 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,9.03,11]-dodecane derives from its tetracyclic structure.