The syntheses and characterizations of two new energetic compounds based on a bis-isoxazole scaffold are presented. The syntheses employ a metal-free [3+2] cycloaddition of an alkyne and a nitrile oxide. In addition, we report the molecular structure of these compounds as determined by single crystal x-ray diffractometry. Both materials have favourable sensitivity properties and low melting points. Their energetic properties indicate potential use as propellant plasticizers.