(N-nitroamino compounds), organic compounds whose molecules contain an —NO2 group bound to a nitrogen atom. Nitramines may be primary, RNHNO2, or secondary, RRʹNNO2 (where R and Rʹ are alkyl or aryl groups).

Monoalkyl nitramines are produced by nitration of N-acylated primary amines (1) or dichloroamines (2) with a nitrating mixture—for example,


Secondary aliphatic nitramines are formed by treating the corresponding amines with a mixture of nitric acid and acetic anhydride or with nitronium fluoboride. Aryl nitramines are synthesized by direct nitration of the corresponding amines or oxidation of diazonium salts.

Aromatic nitramines are usually solids; aliphatic nitramines are liquids or fusible solids. Under the action of acids, primary aliphatic nitramines decompose into the corresponding alcohols and nitrous oxide. Secondary nitramines are resistant to the action of acid even at 100°C, whereas aromatic nitramines undergo various rearrangements.

Upon reaction with alkalies, most primary nitramines yield salts; secondary aliphatic nitramines having α-hydrogen atoms may decompose to amines and aldehydes:

The lower nitramines are extremely explosive. Some nitramines are used as high explosives—for example, trinitro-phenylmethylnitramine (tetryl), cyclotrimethylenetrinitramine (cyclonite), and cyclotetramethylenetetranitramine (octogen).


Khimiia nitro- i nitrozogrupp. Edited by H. Feuer. Moscow, 1972. (Translated from English.)
Overberger, C. G., J.-P. Anselme, and J. G. Lombardino. Organicheskie soedineniia so sviaziami azot-azot. Leningrad, 1970. (Translated from English.)


References in periodicals archive ?
Keshavarz, Approximate prediction of melting point of nitramines, nitrate esters, nitrate salts and nitroaliphatics energetic compounds, J.
The chapters cover the environmental toxicology of munitions-related nitroaromatics and nitramines; pesticides, plant genetics, and biofuels; the influence of pesticide and environmental contaminants on emerging diseases of wildlife; impacts of contaminants and pesticides on biodiversity and ecosystem structure and function; impacts of anthropogenic carbon dioxide and climate change on the biology of terrestrial and marine systems; statistical models in wildlife toxicology; global perspectives; assessing ecological risk; and the global future of wildlife toxicology.
EPA SW-846 Method 8330, "Nitroaromatics and Nitramines by HPLC".
Most of these compounds are nitramines (N-NO2-based), and the total average value of Fcald/Fexptl is more than 1.003.
Zhu, Crystal Density Predictions for Nitramines Based on Quantum Chemistry, J.
They write for chemists working in the field of energetic materials, and for students and others with an interest in the chemistry of nitramines, nitro compounds, nitrate esters, and nitration in general but who have no background in the chemistry of explosives.
Out of various classes of energetic materials, nitramines are ranked at top due to their high energetic properties and that is why technical application of these energetic materials is always useful [2, 3].