Synthesis and Characterization of 1‐Azido‐2‐Nitro‐2‐Azapropane and 1‐Nitrotetrazolato‐2‐Nitro‐2‐Azapropane

Abstract 1‐Azido‐2‐nitro‐2‐azapropane (1) was synthesized in high yield from 1‐chloro‐2‐nitro‐2‐azapropane and sodium azide. 1‐Nitrotetrazolato‐2‐nitro‐2‐azapropane (2) was synthesized in high yield from 1‐chloro‐2‐nitro‐2‐azapropane and silver nitrotetrazolate. The highly energetic new compounds (1 and 2) were characterized using vibrational (IR and Raman) and multinuclear NMR spectroscopy (1H, 13C, 14N), elemental analysis and low‐temperature single crystal X‐ray diffraction. 1‐Azido‐2‐nitro‐2‐azapropane (1) represents a covalently bound liquid energetic material which contains both a nitramine unit and an azide group in the molecule. 1‐Nitrotetrazolato‐2‐nitro‐2‐azapropane (2) is a covalently bound room‐temperature stable solid which contains a nitramine group and a nitrotetrazolate ring unit in the molecule. Compounds 1 and 2 are hydrolytically stable at ambient conditions. The impact sensitivity of compound 1 is very high (<1 J) whereas compound 2 is less sensitive (<6 J).