Synthesis of TKX-50 via 2-Methoxyisopropyl-Protected Diazidoglyoxime as an Insensitive Intermediate

Heun Jong Ha, Bora Kim, Kuktae Kwon, Seung Hee Kim, Chang Woo Cho

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A safe synthesis of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50) has been achieved by using 2-methoxyisopropyl-protected diazidoglyoxime (MIP-DAzG) as an insensitive intermediate. The MIP group acted as a protecting group, which was quantitatively introduced into dichloroglyoxime without the need for any additives, and effectively removed during the course of the cyclization reaction used to construct the 5,5′-bistetrazole-1,1′-diol moiety under acidic conditions. Notably, the sensitivity results obtained for MIP-DAzG were significantly lower than those of the DAzG intermediate used in the previously reported synthesis of TKX-50. Furthermore, the sensitivity studies on MIP-DAzG indicated that the sensitivity of protected DAzG was affected by the steric hindrance around the hydroxyl group in DAzG caused by the protecting group.

Original languageEnglish
Pages (from-to)732-736
Number of pages5
JournalPropellants, Explosives, Pyrotechnics
Volume46
Issue number5
DOIs
StatePublished - May 2021

Keywords

  • Diazidoglyoxime
  • Explosive
  • Insensitivity
  • Protecting group
  • TKX-50

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