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Synlett 2011(14): 2097-2099  
DOI: 10.1055/s-0030-1261169
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

3,6-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazene (BNDD): A Powerful Sensitive Explosive

Philip W. Leonard*a, Colin J. Pollarda, David E. Chaveza, Betsy M. Riceb, Damon A. Parrishc
a Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA
b Army Research Laboratory, Aberdeen Proving Grounds, Aberdeen, MD 20783, USA
c Naval Research Laboratory, Laboratory for the Structure of Matter, Washington, DC 20375, USA
Fax: +1(505)6670500; e-Mail: philipl@lanl.gov;
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Received 23 May 2011
Publikationsdatum:
10. August 2011 (online)

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Abstract

The explosive 3,6-bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazene (BNDD) was synthesized by oxidation of the corresponding diamine using hydrogen peroxide in sulfuric acid with sodium tungstate. The product exhibited detonations during sensitivity testing at low insult; the material is shock and friction sensitive. The synthesis of BNDD should only be pursued by knowledgeable researchers exercising extreme caution.

Key words

explosives - furazan - heterocycles - nitrogen - oxidation

9

CCDC No. 825809

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Preparation of 3,6-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazine (1): Concentrated sulfuric acid (8 mL, 148 mmol) and anhyd sodium tungstate (1.22 g, 74 mmol) were combined in a 50-mL round-bottomed flask and stirred. The flask was suspended in an ice bath. To the acidic solution, 90% hydrogen peroxide solution (4 mL, 148 mmol) was added dropwise. The solution was allowed to equilibrate for 10 min before adding 3,6-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazine, (5; 1.00 g, 4 mmol) portion-
wise and CH2Cl2 (2 mL) to minimize foaming. The bath temperature was raised to 15 ˚C and a Vigreux column with a drying tube was attached. The solution became green then faded to an off-white color at which time sodium tungstate (0.61 g, 37 mmol) and 90% hydrogen peroxide (2 mL, 74 mmol) were added. After stirring for 30 min, the reaction was poured into 250 mL of ice water, stirred for 1 h, and vacuum filtered. The crude product (1 g) was dissolved into MeCN (30 mL), stirred for 10 min, and filtered. H2O (50 mL) was added to the filtrate with stirring and the resulting precipitate collected yielding BNDD (1; 0.9 g, 2.9 mmol) in 70% yield; mp 99 ˚C. ¹³C NMR (DMSO-d 6): δ = 139.7, 152.4, 159.9. IR: 1671, 1587, 1556, 1481, 1088, 1029, 1011, 861, 825, 764 cm-¹. Anal. Calcd for C6N8O8: C, 23.09; N, 35.90. Found: C, 23.13; N, 36.00.