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Synthesis of 5,6‐Di(2‐fluoro‐2,2‐dinitro ethoxy)‐2,3‐Dicyanopyrazine by One–step Nucleophilic Substitution and Its Energetic Properties
Author(s) -
Ma Qing,
Gu Hao,
Lu Huanchang,
Liao Longyu,
Huang Jinglun,
Fan Guijuan,
Li Jinshan,
Liu Dabin
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700737
Subject(s) - nucleophilic substitution , energetic material , detonation , thermal stability , trinitrotoluene , nucleophilic aromatic substitution , explosive material , alkoxy group , crystal structure , nitro , chemistry , triazine , infrared spectroscopy , mass spectrum , nucleophile , crystallography , materials science , medicinal chemistry , organic chemistry , ion , alkyl , catalysis
5,6‐di(2‐fluoro‐2,2,–dinitroethoxy)‐2,3‐dicyanopyrazine was synthesized in a one‐pot process starting from 5,6‐dichloro‐2,3‐dicyanopyrazine. Its structure was fully characterized by 1 H, 13 C, 15 N and 19 F NMR, mass spectroscopy, infrared spectrum as well as elementary analysis. Low‐temperature X‐ray diffraction was employed for analyzing its crystal structure. It exhibits excellent thermal stability (onset m.p. 203 o C, onset dec. 222 o C) which is comparable to those of 1,3,5‐trinitroperhydro‐1,3,5‐triazine (RDX). Different from RDX, it shows good safety properties ( IS >60 J, FS =160 N). Its detonation performance exceed those of 2,4,6‐trinitrotoluene (TNT). The above‐mentioned energetic performance show that it is insensitive and worth further potential applications.