Synthesis of Functionalized Tetrazenes as Energetic Compounds

Abstract

1,4-Bis[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]-1,4-dimethyl-2-tetrazene (12a), 1,4-bis[1-isopropoxycarbonylmethyl-1H-tetrazol-5-yl]-1,4-dimethyl-2-tetrazene (12b), and 1,4-bis[1-carboxymethyl-1H-tetrazol-5-yl]-1,4-dimethyl-2-tetrazene (13) have been synthesized as new nitrogen-rich compounds. The tetrazenes were obtained by oxidation of the corresponding tetrazolylhydrazines using bromine. Moreover, a new method to prepare tetrazolylhydrazines in high yield using 5-bromotetrazoles has been developed. 12a, 12b, and 13 were characterized using vibrational spectroscopy (IR, Raman), mass spectrometry, and multinuclear NMR spectroscopy. The crystal structures of 12a, 12b, and 13 were determined using single crystal X-ray diffraction. Furthermore, the energetic properties of 12a, 12b, and 13 have been investigated using DSC and bomb calorimetric measurements. The sensitivity data toward impact and friction has been determined using BAM methods.

Microwave alkylation of lithium tetrazolate

“…The spectroscopic properties ( 1 H NMR, 13 C{1H} NMR, and MIR) were found to be identical with the ones described in Ref. [39]. …”

Stable heterocumulene monomer in water; Synthesis and polymerization of (meth)acrylates having an isothiocyanate structure

“…Because of a safety reason, this method should not to be applied in a large scale synthesis. Then another method was tried, that is an addition of CS 2 to amine precursors (Scheme ) . 2‐Aminoethyl methacrylate hydrochloride ( 3 ), prepared from methacryloyl chloride ( 1 ) and 2‐aminoethanol, was treated with CS 2 and triethylamine at room temperature, which generated dithiocarbonate intermediate.…”

Time-Domain Terahertz Spectroscopy and Density Functional Theory Studies of Nitro/Nitrogen-Rich Aryl-Tetrazole Derivatives

“…11−13 Pellizzeri et al 35 reported the polymorphic characterization of 5(4-pyridyl)tetrazole using time-domain THz spectroscopy and solid-state DFT. A deliberation for the synthesis of nitro/ nitroamino/azido-substituted aryl tetrazole derivatives, such as 2,6-dinitro-4-(1H-tetrazol-1-yl)aniline (C 7 H 5 N 7 O 4 ) (6), N-(2,6-dinitro-4-(1H -tetrazol-1-yl)phenyl)nitramide (C 7 H 4 N 8 O 6 ) (7), 1-(3,4,5-trinitrophenyl)-1H-tetrazole (C 7 H 3 N 7 O 6 ) (8), and 1-(4-azido-3,5-dinitrophenyl)-1H-tetrazole (C 7 H 3 N 9 O 4 ) (9) are recently reported because these compounds exhibit better energetic properties than TNT and are comparable to RDX. The important parameters are comprised in Table 1.…”