Nitroguanidine

Nitroguanidine

Names
IUPAC name 1-Nitroguanidine
Other names Picrite
Identifiers
CAS Number	556-88-7
ChEBI	CHEBI:39180
ChemSpider	10701
Jmol interactive 3D	Image
PubChem	11174
InChI InChI=1S/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4) Key: IDCPFAYURAQKDZ-UHFFFAOYSA-N InChI=1/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4) Key: IDCPFAYURAQKDZ-UHFFFAOYAN
SMILES NC(N)=N[N+]([O-])=O
Properties
Chemical formula	CH4N4O2
Molar mass	104.07 g/mol
Appearance	Colorless crystalline solid
Density	1.71 g/cm^3
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).
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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

1. 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
2. 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.
3. 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.