Tetrakis(2,2,2-trinitroethyl) orthocarbonate (1) and 2,2,2-trinitroethyl formate (2) were synthesized by the reaction of carbon tetrachloride, respectively chloroform, with the corresponding equivalents of 2,2,2-trinitroethanol and catalytic amounts of anhydrous iron(III)chloride. 2,2,2-Trinitroethyl formal (3) was prepared by the condensation of paraformaldehyde with 2,2,2-trinitroethanol. The compounds were fully characterized by single-crystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and multi-temperature DSC measurements. Due to the positive oxygen balance, the suitability of all three compounds mentioned as potential oxidizers in energetic formulations was investigated and discussed. In addition, the heats of formation of the products were determined experimentally using bomb calorimetric methods. With this value and the experimental (X-ray) density, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. Furthermore, the sensitivity towards impact, friction and electrical discharge was tested using the BAM drop hammer, a friction tester as well as a small-scale electrical discharge device.