Journal of Materials Chemistry A
Page 8 of 10
DOI: 10.1039/C3TA15057G
stirred at 60 oC. To the yellow solution, hydroxylamine-O-
sulfonic acid (1.02 g, 9 mmol) was added over ten minutes, and
the mixture was stirred overnight at 60 oC. The final aqueous
solution was extracted by ethyl acetate (3×40 mL), and then the
combined organic phase was dried over Na2SO4. The solvent was
removed under reduced pressure to give the pure aminated
product 18. Yellow solid (138 mg, 32%). Tdec 275 °C; 1H NMR
(d6-DMSO): δ 6.84 (s, 2H), 6.37, (s, 2H), 13C NMR (d6-DMSO): δ
156.1, 155.5; IR (KBr pellet): υ 3424, 3339, 3229, 1672, 1627,
1557, 1516, 1446, 1404, 1314, 1142, 1087, 873, 793 cm-1;
elemental analysis (%) calcd for C2H4N6O2 (144.09): C, 16.67; H,
2.80; N, 58.32; found: C, 16.67; H, 2.80; N, 57.81.
3-Nitro-N-(2,2,2-trinitroethyl)-1H-1,2,4-triazol-1-amine (19):
White solid (190 mg, 65%). Tdec 151 °C; 1H NMR: δ 8.31 (s, 1H),
7.15 (s, 1H), 4.97 (s, 2H); IR (KBr pellet): 3254, 3154, 3015,
2976, 2886, 1606, 1557, 1508, 1418, 1317, 1300, 1194, 1107,
1015, 841, 801, 656 cm-1; elemental analysis (%) calcd for
C4H4N8O8 (292.12): C, 16.45; H, 1.38; N, 38.36; found: C, 16.54;
H, 1.39; N, 37.29.
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X. Dong and Z. M. Zhou, J Mater Chem A, 2013, 1, 8857. (b) P. Yin,
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3-Nitro-N1-(2,2,2-trinitroethyl)-1H-1,2,4-triazole-1,5-diamine
(20): White solid (233 mg, 76%). Tdec 135 °C; 1H NMR: δ 6.48 (s,
1H), 5.61 (s, 2H), 4.92 (s, 2H); IR (KBr pellet): 3525, 2422, 3252,
3006, 2925, 1649, 1603, 1559, 1410, 1299, 1163, 910, 854, 798,
719 cm-1; elemental analysis (%) calcd for C4H5N9O8 (307.14): C,
15.64; H, 1.64; N, 41.04; found: C, 15.78; H, 1.63; N, 38.80.
Acknowledgements
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The authors gratefully acknowledge the support of ONR
(N00014-12-1-0536); and (N00014-11-AF-0-0002).
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