Nitroguanidine
| |||
| Names | |||
|---|---|---|---|
| IUPAC name
1-Nitroguanidine | |||
| Other names
Picrite | |||
| Identifiers | |||
556-88-7  | |||
| 3D model (Jmol) | Interactive image | ||
| ChEBI | CHEBI:39180 | ||
| ChemSpider | 10701 | ||
| ECHA InfoCard | 100.008.313 | ||
| PubChem | 11174 | ||
| |||
| |||
| Properties | |||
| CH4N4O2 | |||
| Molar mass | 104.07 g/mol | ||
| Appearance | Colorless crystalline solid | ||
| Density | 1.71 g/cm3 | ||
| Melting point | 232 °C (450 °F; 505 K) | ||
| Boiling point | 250 °C (482 °F; 523 K) (decomposes) | ||
| Explosive data | |||
| RE factor | 1.00 | ||
| Hazards | |||
| Main hazards | Explosive | ||
| Related compounds | |||
| Related compounds |
Guanidine Guanidine nitrate | ||
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
verify (what is  ?) | |||
| Infobox references | |||
Nitroguanidine is an organic compound with the formula (NH2)2CNNO2. It is a colorless, crystalline solid that melts at 232 °C and decomposes at 250 °C. It is not flammable and is a low-sensitivity explosive; however, its detonation velocity is high. It is used as a propellant (air bags), fertilizer, and for other purposes.
Manufacture
Nitroguanidine is produced commercially by a two step process starting with the reaction of calcium cyanamide with ammonium nitrate. Via the intermediacy of biguanidine, this ammonolysis step affords the salt guanidinium nitrate. In the second step, the nitrate salt is treated with sulfuric acid, a process that dehydrates the salt and forms the N-N bond.[1]
- [C(NH2)3]NO3 → (NH2)2CNNO2 + H2O
Nitroguanidine can also be generated by treatment of urea with ammonium nitrate. Owing to problems of reliability and safety, this process has not been commerciallized despite its attractive economic features.
Uses
Explosives
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 to avoid.
Pesticides
Nitroguanidine derivatives are used as insecticides, having a comparable effect to nicotine. Derivatives include clothianidin, dinotefuran, imidacloprid, and thiamethoxam.
Biochemistry
The nitrosoylated derivative nitrosoguanidine is often used to mutagenize bacterial cells for biochemical studies.
Structure
Nitroguanidine exists in two tautomeric forms, as a nitroimine (left) or a nitroamine (right). In solution and in the solid state, the nitroimine form predominates (resonance stabilized).[2][3]
References
- ↑ Thomas Güthner, Bernd Mertschenk and Bernd Schulz "Guanidine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_545.pub2
- ↑ Bulusu, S.; Dudley, R. L.; Autera, J. R. (1987). "Structure of nitroguanidine: nitroamine or nitroimine? New NMR evidence from nitrogen-15 labeled sample and nitrogen-15 spin coupling constants". Magnetic Resonance in Chemistry. 25 (3): 234–238. doi:10.1002/mrc.1260250311.
- ↑ Murmann, R. K.; Glaser, Rainer; Barnes, Charles L. (2005). "Structures of nitroso- and nitroguanidine x - ray crystallography and computational analysis". Journal of Chemical Crystallography. 35 (4): 317–325. doi:10.1007/s10870-005-3252-y.