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FOX-7
FOX-7
FOX-7
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FOX-7
Names
Preferred IUPAC name
2,2-Dinitroethene-1,1-diamine
Other names
FOX-7
FOX7
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.130.630 Edit this at Wikidata
EC Number
  • 604-466-1
UNII
  • InChI=1S/C2H4N4O4/c3-1(4)2(5(7)8)6(9)10/h3-4H2
    Key: FUHQFAMVYDIUKL-UHFFFAOYSA-N
  • N/C(N)=C([N+]([O-])=O)\[N+]([O-])=O
Properties
C2H4N4O4
Molar mass 148.08
Appearance Bright yellow crystalline powder[1]
Density 1.885 g cm−3
Melting point 238 °C (460 °F; 511 K) (decomposes)
Soluble in polar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-Dimethylformamide (DMF), and N-Methyl-2-pyrrolidone (NMP)[1]
Hazards
GHS labelling:
GHS01: ExplosiveGHS02: FlammableGHS07: Exclamation mark
Danger
H201, H228, H302
P210, P230, P240, P241, P250, P264, P270, P280, P301+P312, P330, P370+P378, P370+P380, P372, P373, P401, P501
Explosive data
Friction sensitivity >350N[2]
Detonation velocity 8870 m/s at density 1.885 g cm−3 (estimated)
8335 m/s at density 1.756 g cm−3 (measured, small-scale testing)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

FOX-7 or 1,1-diamino-2,2-dinitroethylene (DADNE)[3] is an insensitive high explosive compound. It was first synthesized in 1998 by the Swedish National Defence Research Institute (FOA).[4] According to other information it was synthesized in the USSR in 1990.[citation needed] The name FOX-7 is derived from the acronym of the Swedish Defence Research Agency (FOI), with the I replaced by an X to indicate an explosive, as in RDX and HMX.[5]

FOX-7 is similar to the insensitive chemical compound TATB, which is a benzene ring compound with three amino and three nitro groups.[6] FOX-7 has a two-carbon backbone rather than a benzene ring, but the amino and nitro groups have similar effects in both cases according to published reports on the sensitivity and chemical decay processes of FOX-7.[1] FOX-7 is stoichiometrically identical (but structurally unrelated)[2] to the explosives and propellants RDX and HMX, and therefore produces the same quantity of gas per gram, a key determinant of performance.[1]

By various measures, such as dropped-weight impact, friction force, temperature of ignition, and response to heating under confinement, it is less sensitive than the benchmark explosive RDX, while having performance slightly greater than the same.[2] Its explosive properties appear extremely favorable; in addition to its insensitive properties, the detonation velocity of mixtures of 80% FOX-7 plus binders is as high as Composition B, and nearly pure FOX-7 based plastic bonded explosives are slightly superior to RDX.[7] FOX-7 has been calculated to have a detonation velocity of 8,870 m/s.[8] Charges composed of EVA-coated FOX-7 granules pressed into pellets of 92% theoretical maximum density were found to have a detonation velocity of 7730 m/s, compared to 7630 m/s for a similar RDX/EVA composition, and 5% greater detonation pressure.[2]

FOX-7 is produced as of 2018 by EURENCO Bofors AB of Sweden,[9] having been made in batches up to 7kg in 2001.[10] In laboratory-scale synthesis, material costs were calculated at ~AU$3000/kg (prices in 2002 AUD) using prices from research chemical suppliers. At that time, FOX-7 could be purchased from NEXPLO Bofors AB at SEK3200/kg.[2] Due to its small-scale production, the cost of FOX-7 is relatively high. However, the production is based on commercial starting material and the synthesis is uncomplicated.[11]

FOX-7 is an attractive subject for research and development due to its combination of insensitivity and power. FOX-7 performs similarly to RDX, unlike other insensitive high explosives under investigation, such as TATB, nitrotriazolone, TEX, and 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105). Due to the need for less sensitive munitions, FOX-7 is being investigated at many military research centers,[1] including in Australia, India, the USA, and Sweden.[5][2][9][10]

References

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Further reading

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FOX-7

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FOX-7, chemically known as 1,1-diamino-2,2-dinitroethene or 1,1-diamino-2,2-dinitroethylene (DADNE) (C₂H₄N₄O₄), is a high-performance material developed by the Swedish Defence Research Agency (FOI, formerly FOA) and first reported in 1998. It features a symmetrical molecular structure with two amino groups and two nitro groups attached to an ethene backbone, contributing to its energetic properties while maintaining low sensitivity to impact and friction. This compound is notable for balancing high detonation performance—comparable to established explosives like and —with enhanced safety, making it suitable for in military applications. FOX-7 exhibits a density of 1.86–1.885 g/cm³ and a theoretical detonation velocity of 9090 m/s at maximum theoretical density, surpassing that of RDX (8940 m/s) and NTO (8564 m/s), with a theoretical detonation pressure of 36.6 GPa. Its experimental detonation velocity reaches approximately 7730 m/s at 92% of theoretical maximum density. In terms of sensitivity, it demonstrates an impact height of 110–159 cm (compared to 38 cm for RDX) and friction sensitivity greater than 350 N (versus 120 N for RDX), positioning its insensitivity closer to TATB while offering superior energy output. Thermally, FOX-7 is stable, undergoing phase transitions from α to β at around 116–117°C and β to γ at about 157°C, without a distinct melting point before decomposition. The synthesis of FOX-7 typically involves of a precursor followed by , with optimized methods achieving yields of up to 80% in pilot-scale production. Its low solubility in water and most organic solvents, but high solubility in DMSO, aids in processing, and efforts to produce spherical crystals (average size ~323 μm) have shown to enhance packing density, stability, and overall performance. As an insensitive energetic material, FOX-7 has been explored in composites with other explosives like to further optimize detonation properties and safety for advanced munitions.

Chemical Identity

Nomenclature

FOX-7, chemically known as 2,2-dinitroethene-1,1-diamine, is the for this . It is also referred to by the synonym 1,1-diamino-2,2-dinitroethene. The designation FOX-7 derives from the Swedish Försvarets forskningsanstalt (FOA), the defense research agency where it was developed as the seventh in their series. Commonly abbreviated as DADNE, standing for 1,1-diamino-2,2-dinitroethylene, this name reflects its structural features with two amino groups on one carbon of the ethene backbone and two nitro groups on the adjacent carbon. The molecular formula of FOX-7 is C₂H₄N₄O₄, corresponding to a of 148.08 g/mol. Its is 145250-81-3.

Molecular Structure

FOX-7, chemically known as 2,2-dinitroethene-1,1-diamine, features a central C=C flanked by two amino (-NH₂) groups and two nitro (-NO₂) groups, resulting in a nearly planar with intramolecular hydrogen bonding between the amino hydrogens and nitro oxygens. This hydrogen bonding contributes to the molecule's stability and is evident in the solid state, where the atoms lie approximately in the same plane, with slight twists in the functional groups. The of FOX-7 at is the α-phase, which is monoclinic with P2₁/n and contains four molecules per , arranged in wave-shaped layers held together by intermolecular bonds and van der Waals interactions. The lattice parameters for the α-phase are a = 6.94 , b = 11.23 , c = 7.24 , and β ≈ 91.5°. Upon heating, FOX-7 undergoes phase transitions to the β-phase around 113°C (orthorhombic, similar packing but with altered bonding), the γ-phase at higher temperatures, and the δ-phase near the , each exhibiting distinct lattice expansions and molecular rearrangements. Bond characteristics in FOX-7 reveal effects, with shortened C-N bonds (approximately 1.35–1.40 Å) indicative of partial double-bond character due to delocalization, contributing to its zwitterionic nature where the amino groups act as electron donors and nitro groups as acceptors in a push-pull system. This donor-acceptor electronic structure stabilizes the molecule by distributing charge and enhancing thermal resilience. FOX-7 exhibits between the predominant amino-nitro form (H₂N-C(NO₂)=C(NO₂)-NH₂) and less stable imino-nitrito forms, with the amino-nitro favored in both gas and solid phases due to lower energy and stronger intramolecular hydrogen bonding.

Physical and Chemical Properties

Physical Characteristics

FOX-7 appears as a bright crystalline powder under standard conditions. The theoretical density of FOX-7 is 1.885 g/cm³, determined via powder X-ray diffraction, while experimental densities for single crystals range from 1.86 to 1.87 g/cm³ as measured by pycnometry; for pressed samples, values around 1.76 g/cm³ have been reported to reflect packing efficiency in formulations. FOX-7 exhibits high solubility in polar aprotic solvents such as (DMSO), N,N-dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP), with increasing with temperature in these media; it shows sparing in , , and acetone, limiting its dissolution in protic and less polar solvents. In its typical form, FOX-7 crystallizes as prismatic or rhombohedral particles, often around 30–100 µm in size depending on synthesis and recrystallization conditions; research has focused on modifying these to spherical morphologies via techniques like or methods to enhance and flow properties in energetic formulations. The α-phase is monoclinic ( P2₁/n), while the β-phase is orthorhombic. Reports differ on the exact number and stability of higher polymorphs.

Thermal and Spectroscopic Properties

FOX-7 decomposes at approximately 238 °C without prior melting. The thermal decomposition is exothermic, with an onset temperature around 225 °C and activation energies of 238 kJ/mol and 322 kJ/mol for the two stages; the primary gaseous products include N₂, CO₂, H₂O, and NOₓ species. These decomposition characteristics contribute to FOX-7's balance of stability and energy release, making it suitable for insensitive munitions applications. The compound undergoes reversible solid-solid phase transitions as temperature increases: from the room-temperature α-phase to the β-phase at approximately 80–90 °C, β to γ at about 115 °C, and γ to δ at 155–165 °C, with the latter phase stable until decomposition upon further heating. These transitions are , involving changes in and volume, and have been observed via techniques such as (DSC) and , influencing the material's mechanical and thermal behavior. Note that some transitions may not be visible in all techniques and literature reports vary. Infrared (IR) spectroscopy reveals characteristic vibrational modes for FOX-7, including N-H stretching bands in the 3300–3500 cm⁻¹ region, asymmetric NO₂ stretching at 1550–1600 cm⁻¹, and symmetric NO₂ stretching near 1350 cm⁻¹. These peaks confirm the presence of amino and nitro groups and are used to identify structural forms and phase changes. (NMR) spectroscopy provides insights into the molecular environment: the ¹H NMR spectrum displays broad signals at 8.5–9.5 ppm attributable to the NH₂ protons, reflecting hydrogen bonding effects. The ¹³C NMR shows resonances at approximately 128 ppm and 158 ppm for the two olefinic carbons, consistent with the conjugated C=C bond in the ethene backbone. Ultraviolet-visible (UV-Vis) of FOX-7 exhibits an absorption maximum near 350 nm, arising from π–π* transitions in the involving the nitro and amino substituents. This feature aids in quantitative analysis and monitoring of the compound in solution.

Explosive Performance

Detonation Parameters

FOX-7 demonstrates high explosive performance characterized by a theoretical of 9090 m/s at its theoretical maximum of 1.885 g/cm³. Experimental measurements under small-scale conditions yield a of 8335 m/s at a pressed of 1.756 g/cm³ (with 1.5 wt% phlegmatizer). Another experimental value is 7730 m/s at 92% of theoretical maximum without phlegmatizer. The theoretical detonation pressure for FOX-7 is 36.6 GPa, determined through calculations. This value reflects the material's capacity to generate significant shock waves, essential for applications requiring high . The crystal heat of formation of FOX-7 is -134 kJ/mol. Complementing this, the oxygen balance is -21.6%, signifying a moderate oxygen deficiency that influences efficiency but supports balanced gaseous product formation (primarily CO, H₂O, and N₂). In terms of fragment-driving capability, FOX-7 possesses a Gurney energy of approximately 7.5 km²/s², derived from cylinder expansion tests and comparable to that of (around 7.4 km²/s²). Overall, FOX-7 exhibits superior performance relative to when evaluated by density-compensated relative effectiveness (DCRE ≈ 1.15 versus 's 1.0), accounting for its near-equivalent energy output at slightly lower density.

Sensitivity and Stability

FOX-7 demonstrates exceptional insensitivity to mechanical stimuli, a key attribute that classifies it as a low-hazard energetic material ideal for . Its impact sensitivity, assessed via the BAM fallhammer test (2 kg hammer), is a drop height of 126–159 cm (equivalent to approximately 25–31 J), markedly higher than the 38 cm (about 7.5 J) for , reducing the likelihood of unintended during transport or processing. Similarly, friction sensitivity measured on the BAM friction tester surpasses 350 N for recrystallized material, indicating no reaction under typical handling conditions, compared to 's more responsive 120 N value. Regarding shock sensitivity, FOX-7 single crystals show no under shock compression up to 25 GPa, as evidenced by plate impact experiments and . This elevated threshold, combined with small-scale gap test results showing a 6.22 mm initiation distance (versus 9.33 mm for ), underscores its superior performance in shock-resistant formulations, where smaller initiation distance indicates lower sensitivity. Thermally, FOX-7 remains stable without explosion below 200°C, exhibiting a minimal self-heating rate of less than 0.1°C/min up to 180°C, as determined by accelerating rate calorimetry. The thermal decomposition onset occurs around 221°C, providing a wide safety margin for storage and operational use. Chemically, FOX-7 shows strong resistance to hydrolysis and oxidation, with compatibility tests confirming stability when combined with common binders and additives like TNT. It maintains integrity across a pH range of 4 to 10, minimizing degradation risks in varied environmental conditions. Recent studies (as of 2024) have explored FOX-7 in composites with and other materials to further reduce sensitivity while maintaining performance.

Synthesis

Initial Synthesis

The initial laboratory-scale synthesis of FOX-7, first reported in 1998, utilized as the starting material, which was subjected to with 70% HNO₃ and 98% H₂SO₄ at 0-5°C to yield 4,5-dinitro-2-methylimidazole as the key intermediate. This step is highly exothermic, necessitating rigorous cooling to maintain the low temperature and minimize side reactions leading to polynitroimidazoles or other byproducts. The process continues with treatment of the 4,5-dinitro-2-methylimidazole with aqueous , which cleaves the ring to directly yield FOX-7. The overall yield for this three-step sequence is approximately 50-60%. Purification of the final product involves recrystallization from DMSO or water-acetone mixtures to isolate pure FOX-7 crystals. Initial experiments were conducted on a small scale with batches under 1 g, reflecting the challenges of handling the sensitive intermediates and controlling the reaction conditions in early settings. By , the method had been scaled up successfully to 7 kg batches, marking an important advancement in production feasibility while retaining the core route.

Improved Methods

Since the early , an alternative synthetic route to FOX-7 has been developed involving the of acetamidinium with in an alkaline medium, such as in , to form 2-methyl-4,6-pyrimidinedione as an intermediate, followed by with mixed acids and subsequent . This method achieves an overall yield of approximately 80% for the key intermediate and offers easier isolation of the precursor compared to earlier approaches. Microfluidic crystallization has emerged as a significant advancement, utilizing continuous flow reactors for the recrystallization step via solvent-antisolvent interactions in swirl-shaped chips to enhance product purity. In these systems, FOX-7 is dissolved in DMSO and mixed with , yielding ultrafine FOX-7 particles with purity exceeding 98% and average sizes around 2.4 μm, compared to irregular 10.5 μm particles from traditional beaker methods. This approach reduces crystal defects, improves thermal stability (decomposition temperature increased by 24.6°C), and minimizes safety risks during processing. To optimize explosive performance, morphologies have been achieved through spray-drying and techniques, enabling better control over particle shape and packing . Spray-drying with binders like Viton produces hollow microspheres with shell thicknesses of about 870 nm, while anti-solvent methods using DMSO-acetone mixtures yield spheres with near 1.0 and average diameters of 323 μm, enhancing via improved (up to 1.8 g/cm³). Recent innovations as of 2025, including comparisons of beaker versus microfluidic processes from the Modern Chemistry Research Institute, have demonstrated particle distributions and 98% mass fraction purity, further supporting and gains. Environmental enhancements include the of spent acids without yield loss, reducing acid waste in the process while maintaining >90% overall efficiency. Continuous processes, such as microfluidic flow reactors, facilitate scale-up to industrial levels through modular numbering-up and consistent .

History and Development

Discovery

1,1-Diamino-2,2-dinitroethene, known as FOX-7, was first synthesized in 1998 by a team of researchers at the Swedish Defence Research Establishment (FOA, now the Swedish Defence Research Agency, FOI), led by Nikolai V. Latypov, Jan Bergman, Abraham Langlet, Ulf Wellmar, and Ulf Bemm. The compound emerged unexpectedly during reactions of heterocyclic precursors, such as and related imidazolones, yielding the target molecule upon treatment with aqueous . The development of FOX-7 was driven by the need for insensitive high explosives that could serve as safer alternatives to conventional materials like and , maintaining comparable performance while minimizing risks from accidental initiation. Prior to full synthesis, theoretical predictions based on quantum chemical calculations suggested that FOX-7 would exhibit a high and pressure similar to , coupled with significantly lower sensitivity. The initial publication detailing the synthesis and basic reactions appeared in 1998 as an FOI , followed by a peer-reviewed article in Tetrahedron. Early characterization through small-scale trials confirmed the anticipated properties, demonstrating low impact and friction sensitivity alongside a exceeding 8,000 m/s in preliminary tests. The designation "FOX-7" derives from FOI's experimental explosive nomenclature, where "FO" represents the agency, "X" denotes explosive (analogous to ), and "7" marks it as the seventh compound in the series.

Commercial Production

Commercial production of FOX-7 began in 2001 by in , where it was manufactured in pilot-scale batches of up to 7 kg, with nearly 1,000 kg produced overall through 1 to 3 batches per day. This initial scale-up was enabled by improvements in the synthesis process, achieving an 80% molar yield. Early production costs were high due to the small-scale operations, exceeding €3,000 per kg, which restricted broader industrial adoption despite the material's favorable properties. Due to small-scale production, FOX-7 costs remain relatively high compared to conventional explosives like , though potential reductions are expected with increased scale. Global research interest grew rapidly in the early , with involvement from institutions such as the Defence Science and Technology Organisation (DSTO) in , which issued a comprehensive report on FOX-7's properties and potential. The (NSWC) Indian Head Division in the United States conducted extensive studies on its structural response, sensitivity, and high-pressure behavior, often providing high-purity samples for collaborative experiments. Similarly, India's (DRDO) supported research on FOX-7's spectroscopic and explosive characteristics through funded projects. These efforts included international collaborations focused on (IM) testing to evaluate FOX-7's performance under various stimuli. Research in has explored FOX-7 in experimental composites to enhance insensitivity and address cost barriers through blended systems. As of 2025, Eurenco Bofors AB in remains the primary commercial producer of FOX-7, while the Xi'an Modern Chemistry Research Institute in supplies high-purity FOX-7 (≥98%) for domestic and research applications. The high production costs continue to limit widespread adoption, prompting a strategic emphasis on FOX-7-based composites that enhance overall material performance without requiring large quantities of the pure compound. For regulatory compliance, FOX-7 is registered with the (ECHA) under EC number 604-466-1, facilitating safe handling and transport in contexts.

Applications

Military Formulations

FOX-7 serves as a primary filler in (PBX) compositions for warheads in missiles and , often replacing to balance high performance with reduced sensitivity. Typical formulations include approximately 70% FOX-7 combined with 30% binder, such as (EVA) or polyethylene wax, achieving theoretical maximum densities (TMD) of 92-95% for pressed pellets. These PBX variants exhibit velocities around 8110 m/s and pressures of 25.1 GPa, making them suitable for main charge applications in . In (IM) design, FOX-7 formulations comply with STANAG 4439 criteria, demonstrating low reactivity in thermal threats through fast and slow trials. Tests show mild burning responses, classified as Type V or lower violence, which minimizes catastrophic detonation risks. This compliance stems from FOX-7's inherent thermal stability, enabling its use in PBX with energetic binders like polyGLYN for enhanced safety in operational environments. For applications, FOX-7 enhances jet penetration in liners, leveraging its theoretical exceeding 8500 m/s in optimized blends to achieve armor defeat capabilities comparable to traditional RDX-based fills. Its integration into fragmenting and slow-stretching jet warheads has been evaluated via cylinder expansion tests, confirming reliable performance akin to while maintaining insensitivity. Blends such as 80% FOX-7 with 20% boost overall energy output for high-performance needs. These combinations retain FOX-7's core parameters, with velocities near 8100 m/s, to support versatile payloads. The primary advantages of FOX-7 in formulations include diminished accidental risks during storage and transport, aligning with global requirements to enhance troop safety and logistics reliability. By the 2010s, FOX-7 had been incorporated into munitions by Swedish and Australian defense programs, with pilot-scale production at NEXPLO AB supporting booster and integrations. As of 2025, production remains at pilot scale by EURENCO AB (successor to NEXPLO), with incorporation primarily in research and select booster applications.

Research Composites

Research into FOX-7-based nanocomposites and hybrids has focused on enhancing performance, sensitivity, and overall energetic properties through advanced fabrication methods. One prominent approach involves the creation of FOX-7/ core-shell nanocomposites via spray-drying, which enables precise control over particle morphology and interfacial interactions. These composites show improved mechanical sensitivity compared to pure . This improvement stems from the synergistic effects of FOX-7's high density and 's reactivity, leading to more uniform energy release and reduced voids in the microstructure. Metalized variants, such as FOX-7/Al microparticles incorporating 20-30% aluminum, have been explored for thermobaric applications to amplify blast effects. Fabricated through spray-drying with binders like Viton, these particles promote efficient aluminum combustion post-detonation, resulting in a 15% increase in blast energy output relative to non-metalized FOX-7 counterparts. The aluminum coating enhances and oxidation rates, making these hybrids suitable for scenarios requiring prolonged pressure waves without compromising FOX-7's inherent insensitivity. Encapsulation strategies using zeolitic imidazolate framework-8 (ZIF-8) have shown promise in tailoring FOX-7's initiation behavior. Nano-sized FOX-7/ZIF-8 composites, prepared via liquid-assisted mechanochemical synthesis, facilitate faster detonation initiation by accelerating decomposition kinetics while simultaneously reducing mechanical sensitivity—critical impact height increases notably compared to pristine FOX-7. This dual benefit arises from ZIF-8's porous structure, which confines FOX-7 particles and mitigates hotspot formation during shock loading. In -based thermobaric formulations, incorporating 10-20% FOX-7 has demonstrated significant advantages in afterburn dynamics. These additions shorten afterburn delay by promoting aluminum particle ignition and , while enhancing sustained through optimized release profiles—total impulse rises by at least 15% in optimized blends. The lower FOX-7 content (around 15%) strikes a balance between maintaining high and minimizing sensitivity, outperforming pure /Al systems in confined tests. Recent studies from 2023 to 2025 have advanced FOX-7 processing via microfluidic techniques, yielding particles with uniform (PSD) typically below 5 μm. These methods ensure consistent morphology, reducing defects and enabling scalable production for high-performance applications. Additionally, investigations into FOX-7/CL-20 compatibility for hybrid propellants confirm excellent and mechanical stability, with cocrystal or composite forms exhibiting cohesive energy densities that support 10-20% performance gains in and without heightened sensitivity. Overall, these research efforts aim to tailor FOX-7 morphology for targeted enhancements, such as 10-20% improvements in detonation parameters, while incorporating environmental impact assessments to evaluate decomposition byproducts and lifecycle sustainability. Such hybrids prioritize reduced ecological footprints alongside superior energetic output, aligning with broader goals in insensitive munitions development.

References

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