Energetic 1,2,5-Oxadiazolo-Pyridazine and its N-Oxide

Article abstract of DOI:10.1002/chem.201703930

Achieving an energetic compound, which exhibits high performance and insensitivity, is important in the field of energetic materials and remains a major challenge. Herein, we found that oxidation of 4,7-diaminopyridazino[4,5-c]furoxan (5) with a mixture of 50 % hydrogen peroxide and trifluoroacetic anhydride gave 6-amino-7-nitro-[1,2,5]oxadiazolo[3,4-c]pyridazine (7) and its N-oxide derivative (8). The oxidation of 5 with hypofluorous acid (HOF) was also studied. Compound 8 displayed an energetic performance compared to triaminotrinitrobenzene (TATB) and insensitive properties (impact sensitivity (IS) 36 J and friction sensitivity (FS)>360 N). Such excellent properties make 8 attractive for high-performance applications, in which insensitivity is important.

Full text of DOI:10.1002/chem.201703930

A Journal of
Accepted Article
Title: Energetic 1,2,5-oxadiazolo-pyridazine and its N-oxide
Authors: Jean'ne Shreeve, Yongxing Tang, Chunlin He, Gregory H.
Imler, and Damon Parrish
This manuscript has been accepted after peer review and appears as an
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To be cited as: Chem. Eur. J. 10.1002/chem.201703930
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Energetic 1,2,5-oxadiazolo-pyridazine and its N-oxide
Yongxing Tang,[a] Chunlin He, [a] Gregory H. Imler,[b] Damon A. Parrish,[b] and Jean'ne M. Shreeve*[a]
Dedication ((optional))
Abstract: Achieving an energetic compound which exhibits high
diaminopyridazino[4,5-c]furoxan (5) with HOF or a mixture of 50%
hydrogen peroxide and trifluoroacetic anhydride which does not
undergo the expected oxidation reaction.
performance and insensitivity is important in the field of energetic
materials and remains
a major challenge. Here we find that
oxidation of 4,7-diaminopyridazino[4,5-c]furoxan (5) with a mixture of
50% hydrogen peroxide and trifluoroacetic anhydride gives rise to 6-
amino-7-nitro-[1,2,5]oxadiazolo[3,4-c]pyridazine (7) and its N-oxide
derivative (8). The oxidation of 5 with hypofluorous acid (HOF) was
also studied. Compound
8 displays an energetic performance
compared to TATB and insensitive properties (IS: 36 J and FS: >360
N). Such excellent properties make 8 attractive for high performance
applications where insensitivity is important.
With the advent of numerous strategies for design and synthesis
of high energy density materials, the challenging optimum
balance between detonation performance and sensitivity has
come into focus.[1] Most well-established strategies involving
enforced layer-by-layer stacking,[2] intramolecular hydrogen
bonds,[3] 3D metal organic frameworks (MOFs),[4] and
cocrystallization[5] show reasonable prospects. From the view
point of synthetic methodology, the introduction of a nitro group
while maintaining the stability of the molecule is an efficient
method. The synthesis of novel energetic compounds containing
vicinal C−NH2/C−NO2 functionalities gives an unprecedented
entry to extend the variety of insensitive energetic compounds
by condensation of nitroacetonitrile with the diazonium moiety.[6]
Meanwhile, the incorporation of the N-oxide component has
been shown to be an efficient method to improve the detonation
performance.[7]
Based on previous oxidation studies using HOF[8] or a mixture
of 50% hydrogen peroxide and trifluoroacetic anhydride,[7a, 7g] we
selected 4,7-diaminopyridazino[4,5-c]furoxan (5) as the
substrate, which could be converted to the nitro substituted
compound A (Scheme 1). Compound A had been discussed
theoretically, and showed promising properties in the application
of solid composite propellants.[9] During our attempts to
synthesize A through the oxidation reaction of 5 (Scheme 1) with
different oxidizing reagents, we quite surprisingly found the
formation of 6-amino-7-nitro-[1,2,5]oxadiazolo[3,4-c]pyridazine
(7) and its N-oxide (8). Both of them comprise a five-membered
ring fused to a six membered ring having vicinal C−NH2/C−NO2
groups, which showed high stability and insensitive properties.
Now we describe these new findings involving oxidation of 4,7-
Scheme 1. Synthesis of 6-9
Initially,
4,7-diaminopyridazino[4,5-c]furoxan
(5)
was
synthesized based on the literature.[10] Nitration of cyanoacetic
acid (1) with a mixture of 100% nitric acid and trifluoroacetic acid
gave 3,4-cyanofuroxan (2) which when reacted with hydrazine
monohydrate resulted in the intermediate 3-cyanofuroxan-4-
carbamidrazone (3). Compound 3, when treated with acetic acid,
gave rise to 4,7-diaminopyridazino[4,5-c]furoxan diacetate (4).
Finally, 4,7-diaminopyridazino[4,5-c]furoxan (5) was synthesized
by neutralization of 4 with solid sodium carbonate.
Two different common oxidants were used in attempts to
introduce the nitro group into 5 which would enhance the density
thus improving the detonation performance. When hypofluorous
acid
(HOF)
was
the
oxidizer,
4-cyano-3-(N'-
nitrocarbamimidoyl)furoxan (6) was isolated. However, with a
mixture of 50% hydrogen peroxide and trifluoroacetic anhydride,
two novel fused heterocyclic rings, 6-amino-7-nitro-
[1,2,5]oxadiazolo[3,4-c]pyridazine (7) and its N-oxide derivative
(8) were formed and isolated. These products may result from
complex oxidation reactions with the concomitant rearrangement
of the furoxan ring.[11]In addition, 4,7-diaminopyridazino[4,5-
c]furoxan trifluoroacetate (9) was also formed at a high yield.
[a]
[b]
Dr. Y. Tang, Dr. C. He, Prof. Dr. J. M. Shreeve
Department of Chemistry, University of Idaho, Moscow, Idaho,
83844-2343, United States
Fax: (+1) 208-885-9146
E-mail: jshreeve@uidaho.edu
The structures of 6
̶
9 were confirmed by single crystal X-ray
diffraction analysis.
Suitable crystals of 6
̶
8 for X-ray diffraction analysis were
Dr. G. H. Imler, Dr. D. A. Parrish
obtained by slow evaporation from a solution of 6 in acetonitrile
and a solution of 7 or 8 in ethyl acetate/hexane, respectively.
Compound 6 crystallizes in the orthorhombic space group Pna21
with a crystal density of 1.813 g cm–3 at 150 K. The crystal
asymmetric unit consists of two independent molecules (Z = 8) is
shown in Figure 1. The parameters of the two molecules in the
Naval Research Laboratory, 4555 Overlook Avenue, Washington,
D.C. 20375, United States
Supporting information for this article is given via a link at the end of
the document.((Please delete this text if not appropriate))
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crystal agree well with each other. The largest difference is 0.08
Å in the N-oxide moiety (N13-O14: 1.261 (5) Å and N27-O28:
1.179 (5) Å).The details are given in the Supporting Information.
In addition, one cyano group is located in the same plane with
furoxan with a torsion angle N10-C9-C8-N11 of 179.8o, while the
other cyano group is twisted out of the furoxan ring with a torsion
angle N24-C-23-C22-N25 of 12.3o.
vs. 1.376(3) Å in 7; N7-N8/N21-N22: 1.290(7)/1.309(7) Å in 8 vs.
1.270(2) Å in 7). The molecules of 8 in the crystal form an
extensive network of hydrogen bonds, especially, the adjacent
nitro group and the amino group form intramolecular H-bonds
via N(6)-H(6B)...O(2) and N(20)-H(20B)...O(16), which is one of
the main reasons for stabilizing the molecules and increasing
the density.
Figure 1. Molecular structure of 6 (drawn with 50% probability)
Figure 3. Molecular structure of 8 (drawn with 50% probability)
Compound 7 crystallizes in the monoclinic space group Cc
and has a calculated density of 1.822 g cm–3 at 150 K (Figure 2).
The bond lengths and the bond angles on the furazan ring and
pyrazine ring are between typical C–N/N–N single and C=N/N=N
double bonds due to the aromaticity. Among them, the bond
lengths of N8-C9 and N7-N8 are 1.376(3) and 1.270(2) Å,
respectively. In the structure, there are three types of hydrogen
bonds including an intramolecular hydrogen bond (N6-H6A…O2)
and two intermolecular hydrogen bonds (N6-H6A…O11 and N6-
H6B…N12).
Since 7 and 8 may find application in the field of energetic
materials, their properties including thermal stability, detonation
performance and sensitivities were studied. The results are
given in Table 1. The onset decomposition temperature of 7 and
o
8 are 186 and 175 C, respectively. The measured density by a
gas pycnometer for 7 is 1.79 g cm-3. As expected, the
introduction of the N→O moiety increases the density; 8 is at
1.84 g cm-3. The gaseous state heats of formation of both
compounds were calculated using G2 method. The solid state
heats of formation were predicted based on the literature.[12] The
values for 7 and 8 are 417.8 and 368.7 kJ mol-1, respectively.
Table 1. Physicochemical and energetic properties of compounds
7 ̶ 8
compared with TATB
ρ[a]
[e]
Dv [b]
P[c]
∆Hf[d]
Tdec
IS[f]
FS[g]
(gcm
(m/s)
(GPa)
(kJ/mol)/(kJ/g)
(oC)
(J)
(N)
3
)
7
8
1.79
1.84
1.93
8396
8695
8504
29.4
32.9
31.7
417.8/2.29
368.7/1.86
-154.2/-0.60
186
175
350
>50
36
>360
>360
353
TATB
50
Figure 2. Molecular structure of 7 (drawn with 50% probability)
[a] Density measured by a gas pycnometer at 25 °C; [b] Calculated detonation
velocity; [c] Calculated detonation pressure; [d] Calculated molar enthalpy of
formation in solid state; [e] Temperature of decomposition (onset); [f] Impact
sensitivity; [g] Friction sensitivity.
Compound 8 crystallizes in the orthorhombic space group
Fdd2 and has a calculated density of 1.909 g cm–3 at 150 K. As
can be seen in Figure 3, the crystal asymmetric unit also
consists of two independent molecules (Z = 32). In the two
molecules, the amino groups, the nitro groups and the fused
heterocyclic ring attached thereto lie in one plane. The bond
lengths of the N-oxide moiety are 1.253(6) (N22-O23) and
1.255(6) (N8-O9) Å, respectively. In comparison with 7, the
presence of the N→O moiety in 8 increases the neighboring
bond lengths. (N8-C10/N22-C24, viz., 1.414(7)/1.392(8) Å in 8
The detonation velocity and pressure were calculated by
using EXPLO5 V6.01 code.[13] Compound 7 is calculated to have
a detonation velocity of 8396 m s-1 and a detonation pressure of
29.4 GPa. In comparison, 8 has a better detonation performance
with a detonation velocity of 8695 m s-1 and a detonation
pressure of 32.9 Gpa, which are superior to those of the
traditional insensitive explosive, TATB.
For initial safety considerations, the impact sensitivity and
friction sensitivity were tested.[14] As shown in Table 1, both of 7
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8: Red solid (0.25 g, 21% yield). Td (onset): 175 oC. 1H NMR(d6-DMSO): δ
10.29 (s, 1H), 9.80 (s, 1H) ppm. 13C NMR (d6-DMSO): δ 167.5, 156.0,
144.0, 108.9 ppm. IR (KBr): ෤ 3413, 3303, 1629, 1543, 1499, 1457, 1425,
1384, 1353, 1285, 1239, 1147, 992, 908, 808, 771,672, 569 cm-1.
Elemental analysis for C4H2N6O4 (198.10): Calcd C 24.25, H 1.02, N
42.42 %. Found: C 24.82, H 1.17, N 42.34 %.
and 8 are insensitive. The impact sensitivity of 7 is more than 50
J, while the impact sensitivity of 8 is 36 J. Both have friction
sensitivity of > 360 N.
In summary, the oxidation of ring system (5) was studied. By
using hypofluorous acid (HOF), a ring-opening product (6) was
formed, while using a mixture of 50% hydrogen peroxide and
trifluoroacetic anhydride led to the formation of two novel fused
compounds 7 and 8. Both of them show good detonation
properties; especially the detonation performance of 8 is better
than that of TATB while meanwhile it exhibits low sensitivities (IS:
36 J; FS: >360 N). This attractive oxidation reaction may provide
a promising route for constructing new fused rings with excellent
properties. The detailed mechanism and further studies along
these findings are currently under study in our laboratories.
9·H2O: Yellow crystals (1.07 g, 60% yield). Tm: 94 oC. Td (onset): 170 oC. 1H
NMR (d6-DMSO): δ 10.08 (br), 8.13-8.89 (m) ppm. 13C NMR (d6-DMSO):
δ 157.1, 154.9, 152.5, 148.8, 110.2, 108.7 ppm. IR (KBr): ෤ 3433, 3410,
3297, 1697, 1669, 1612, 1473, 1435, 1354, 1193, 1157, 1069, 1044, 840,
797, 760, 726, 706, 689, 637, 588, 555 cm-1. Elemental analysis for
C6H7F3N6O5 (300.15): Calcd C 24.01, H 2.35, N 28.00 %. Found: C 24.01,
H 2.45, N 28.19 %.
Acknowledgements ((optional))
Experimental Section
This work was supported by the Office of Naval Research
(N00014-16-1-2089) and the Defense Threat Reduction Agency
(HDTRA 1-15-1-0028). We are also grateful to the M. J.
Murdock Charitable Trust, Reference No.: 2014120:
MNL:11/20/2014 for funds supporting the purchase of a 500
MHz NMR spectrometer. We thank Prof. Richard V. Williams
and Dr. Gang Zhao for the discussion of mechanism.
Caution! Compounds 7 and 8 are potential energetic materials. Although
we have had no difficulty in handling these compounds during the
synthetic procedure, personal protective equipment such as leather
gloves, blast shields and safety glasses should be used at all times.
Synthesis of 4-cyano-3-(N'-nitrocarbamimidoyl)furoxan (6)
A 20% fluorine mixture (in gaseous nitrogen) was bubbled through a
mixture of acetonitrile (40 mL) and water (4 mL) at -15 oC in a dry-ice
bath for 0.5 h. The solution was added to a suspension of 5 (0.25 g, 1.5
mmol) in acetonitrile (2 mL). The reaction mixture was stirred at 0 oC for
0.5 hour and the solvent was removed by air. The residue was added to
water (30 mL), the precipitate was filtered to give a crude product, 6. The
pure product could be obtained by slow evaporation of the solution of 6 in
acetonitrile. Colorless solid (0.15 g, 52% yield). Tm: 158 oC. Td (onset): 162
oC. 1H NMR: δ 9.79 (s, 1H), 9.78 (s, 1H) ppm. 13C NMR: δ 149.7, 134.0,
110.1, 107.5 ppm. IR (KBr): ෤ 3382, 3283, 3175, 2245, 1667, 1615, 1570,
1470, 1381, 1264, 1242, 1107, 1087, 1027, 922, 851, 808, 780. 737, 677,
655 cm-1. Elemental analysis for C4H2N6O4 (198.10): Calcd C 24.25, H
1.02, N 42.42 %. Found: C 24.54, H 1.08, N 42.41 %.
Keywords: energetic materials • furoxan • furazan • pyridazine •
N-oxide
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Synthesis of 6-amino-7-nitro-[1,2,5]oxadiazolo[3,4-c]pyridazine (7),
6-amino-7-nitro-[1,2,5]oxadiazolo[3,4-c]pyridazine 4-oxide (8), and
4,7-diaminopyridazino[4,5-c]furoxan trifluoroacetate (9)
̶
̶
̶
̶
Trifluoroacetic anhydride (4 mL, 28 mmol) was added dropwise to a
slurry of 50% hydrogen peroxide (1.3 mL, 25 mmol) in methylene
chloride (20 mL) with stirring at <10 oC. Compound 5 (1.0 g, 5.9 mmol)
was added at 0 oC and stirred for 30 min and continued for 10 hours at
room temperature. The solvent was removed and the concentrated
solution was added to water (60 mL). The solution was extracted with
ethyl acetate (20 mL × 3). The combined organic phase was dried over
anhydrous magnesium sulfate and the solvent was concentrated. The
residue was separated by column chromatography (EtOAc/n-hexane = 1 :
4) to give 7 and 8. The water phase was evaporated slowly to give 9 as
yellow crystals.
̶
̶
̶
̶
̶
̶
̶
̶
̶
7: Brown solid (0.11 g, 10% yield). Td (onset): 186 oC. 1H NMR (d6-DMSO):
δ 8.81 (s, 1H), 8.40 (s, 1H) ppm. 13C NMR (d6-DMSO): δ 161.5, 152.6,
136.0, 106.7 ppm. IR (KBr): ෤ 3416, 1637, 1561, 1465, 1403, 1354, 1303,
1255, 1140, 986, 950, 918, 790, 764, 717, 675, 647 cm-1. Elemental
analysis for C4H2N6O3 (182.10): Calcd C 26.38, H 1.11, N 45.09 %.
Found: C 25.96, H 1.22, N 46.15 %.
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COMMUNICATION
The oxidation reactions of 4,7-
Y. Tang, C. He, G. H. Imler, D. A.
diaminopyridazino[4,5-c]furoxan
(5)
Parrish, J. M. Shreeve*
gave unexpected products. The
oxidant products, 6-amino-7-nitro-
[1,2,5]oxadiazolo[3,4-c]pyridazine (7)
and its N-oxide derivative (8) exhibit
good detonation performance and
insensitive properties, which may find
potential application in insensitive
energetic materials.
Page No. – Page No.
Energetic 1,2,5-oxadiazolo-pyridazine
and its N-oxide
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