Nitroguanidine

Nitroguanidine
IUPAC name 1-Nitroguanidine
Other names Picrite
Identifiers
CAS number	556-88-7 Y
PubChem	11174
ChemSpider	10701 Y
ChEBI	CHEBI:39180 Y
Jmol-3D images	Image 1
SMILES NC(N)=N[N+]([O-])=O
InChI InChI=1S/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4) Y Key: IDCPFAYURAQKDZ-UHFFFAOYSA-N Y InChI=1/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4) Key: IDCPFAYURAQKDZ-UHFFFAOYAN
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Manufacture

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]

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.

Pesticides

Nitroguanidine and its 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 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]

References

1. ^ Strecker, A (1861). "Untersuchungen über die chemischen Beziehungen zwischen Guanin, Xanthin, Theobromin, Caffein und Kreatinin". Annalen der Chemie und Pharmacie 118 (2): 151–177. doi:10.1002/jlac.18611180203. 
2. ^ Axt (August 1, 2007). "Nitroguanidine: from sulphamic acid and urea". Sciencemadness Discussion Board. http://www.sciencemadness.org/talk/viewthread.php?tid=8911. 
3. ^ 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. 
4. ^ 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.