| Nitroguanidine | |
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1-Nitroguanidine |
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Other names
Picrite |
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| Identifiers | |
| CAS number | 556-88-7 |
| PubChem | 11174 |
| ChemSpider | 10701 |
| ChEBI | CHEBI:39180 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | CH4N4O2 |
| Molar mass | 104.07 g/mol |
| Appearance | Colorless crystalline solid |
| Melting point |
232 °C, 505 K, 450 °F |
| Boiling point |
250 °C (decomp.) |
| Hazards | |
| EU Index | Not listed |
| Main hazards | Explosive |
| Related compounds | |
| Related compounds | Guanidine Guanidine nitrate |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Nitroguanidine is a chemical compound. It is a colorless, crystalline solid. It melts at 232 °C and decomposes at 250 °C. It is not flammable and is an extremely low sensitivity explosive; however, its detonation velocity is high.
Contents |
Nitroguanidine is manufactured from guanine, a naturally-occurring substance typically found in the excrement of bats and birds (guano). Guanine is extracted from the droppings and is then oxidized to form guanidine.[1] Guanidine is then nitrated to form nitroguanidine. The detailed process used to perform industrial-scale synthesis is considered proprietary and is not available for public release. A laboratory synthesis involves the fusion of sulfamic acid with urea, followed by nitration of the formed guanidine sulfate.[2]
Nitroguanidine is used as an explosive propellant, notably in triple-base smokeless powder. The nitroguanidine reduces the propellant's flash and flame temperature without sacrificing chamber pressure. These are typically used in large bore guns where barrel erosion and flash are particularly important.
Nitroguanidine and its derivatives are used as insecticides, having a comparable effect to nicotine. Derivatives include clothianidin, dinotefuran, imidacloprid, and thiamethoxam.
The nitrosoylated derivative nitrosoguanidine is often used to mutagenize bacterial cells for biochemical studies.
Nitroguanidine can exist in distinct tautomeric forms, as a nitroimine (left) or a nitroamine (right). In solution and in the solid state, the nitroimine form predominates.[3][4]