Synthesis, disproportionation and hydrolysis reactions of 3-amino-4-hydroxyaminoximinofurazan

Lianjie Zhai, Bozhou Wang*, Huan Huo, Hui Li, Yanan Li, Xinping Huang, Ning Liu, Xuezhong Fan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


A novel energetic intermediate 3-amino-4-hydroxyaminoximinofurazan (DOAF) was synthesized from 3-amino-4-amidoximinofurazan (DAOF) via diazotisation and oximation reactions with a total yield of 61.8%, and its structure was characterized by NMR, IR, MS and elemental analysis. The main factors for the oximation reaction were thoroughly studied, and the optimum reaction conditions were found to be as follows: the materials ratio n(ACOF):n(NH2OH·HCl):n(CH3ONa) was 1:2:3, reaction temperature 30°C, and reaction time 2 h with a yield of 86.5%. It was found that 3-amino-4-hydroxyaminoximinofurazan (DOAF) was disproportionated to obtain two compounds under alkaline condition, which were identified as 3-amino-4-nitrosoximinofurazan potassium salt and DAOF. Moreover, DOAF was hydrolyzed to give a new product in acidic aqueous solution, which was identified as 3-amino-4-(N-hydroxyamido)furazan. The single crystal of K(DNOF)·H2O was obtained and its crystal belong to monoclinic system, space group is P2(1)/c, cell parameters are a=0.7639(19) nm, b=0.7034(17) nm, c=1.436(4) nm, α=90°, β=101.025(3)°, γ=90°, V=0.7573(3) nm3, Z=4, Dc=1.870 g·cm-3, μ=0.695 mm-1, F(000)=432, R1=0.0349 and wR2=0.1027.

Original languageEnglish
Pages (from-to)1755-1761
Number of pages7
JournalChinese Journal of Organic Chemistry
Issue number8
StatePublished - Aug 2013
Externally publishedYes


  • 3-amino-4-hydroxyaminoximinofurazan
  • Crystal structure
  • Disproportionation
  • Energetic intermediate
  • Hydrolysis
  • Synthesis


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