Nitroguanidine

Names

IUPAC name

1-Nitroguanidine

Other names

Picrite

Identifiers

CAS Number

556-88-7^Y

3D model (Jmol)

CHEBI:39180^Y

10701^Y

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

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/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

Guanidine
Guanidine nitrate

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

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.

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.

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.

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.

Nitroguanidine 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 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).

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