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{{chembox
| Watchedfields = changed
| verifiedrevid = 441076766
| ImageFile = FOX7.png
| ImageSize = 150px
| PIN = 2,2-Dinitroethene-1,1-diamine
| OtherNames = FOX-7 FOX7
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 145250-81-3
| ChemSpiderID = 467536
| PubChem = 536770
| EC_number = 604-466-1
| UNII = 3B2KYV7C3F
| StdInChI = 1S/C2H4N4O4/c3-1(4)2(5(7)8)6(9)10/h3-4H2
| StdInChIKey = FUHQFAMVYDIUKL-UHFFFAOYSA-N
| SMILES = N/C(N)=C([N+]([O-])=O)\[N+]([O-])=O
}}
|Section2={{Chembox Properties
| Formula = C2H4N4O4
| MolarMass = 148.08
| Appearance = Bright yellow crystalline powder<ref name="Anniyappan" />
| Density = 1.885 g cm−3
| MeltingPtC = 238
| MeltingPt_notes = ([[Chemical decomposition|decomposes]])
| BoilingPt =
| Solubility = Soluble in polar aprotic solvents such as [[DMSO|dimethyl sulfoxide (DMSO)]], [[N,N-Dimethylformamide|N,N-Dimethylformamide (DMF)]], and [[N-Methyl-2-pyrrolidone|N-Methyl-2-pyrrolidone (NMP)]]<ref name="Anniyappan" />
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS01}}{{GHS02}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|201|228|302}}
| PPhrases = {{P-phrases|210|230|240|241|250|264|270|280|301+312|330|370+378|370+380|372|373|401|501}}
}}
|Section6={{Chembox Explosive
| ShockSens =
| FrictionSens = >350N<ref name="Lochert" />
| DetonationV = 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)
| REFactor =
}}
}}

'''FOX-7''' or '''1,1-diamino-2,2-dinitroethylene''' '''(DADNE)'''<ref>US Patent 6340780 - Method of preparing salts of dinitromethane</ref> is an [[Insensitive munition#Insensitive high explosives|insensitive high explosive]] compound. It was first synthesized in 1998 by the [[Swedish National Defence Research Institute]] (FOS).<ref name="dsto">Bemm, U.; Östmark, H. (1998) "1,1-Diamino-2,2-dinitroethylene: a Novel Energetic Material with Infinite Layers in Two Dimensions". ''Acta Cryst'' '''C54''': 1997-1999. {{doi|10.1107/S0108270198007987}}.</ref> The name FOX-7 is derived from the acronym of the [[Swedish Defence Research Agency|Swedish Defence Research Agency (FOI)]], with the ''I'' replaced by an ''X'' to indicate an explosive, as in [[RDX]] and [[HMX]].<ref name=":0">{{Citation|last1=Viswanath|first1=Dabir S.|title=FOX-7 (1,1-Diamino-2,2-Dinitroethylene)|date=2018|url=https://doi.org/10.1007/978-94-024-1201-7_3|work=Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties|pages=101–139 |place= Dordrecht|publisher=Springer Netherlands|doi=10.1007/978-94-024-1201-7_3|isbn=978-94-024-1199-7|access-date=2021-01-25|last2=Ghosh |first2=Tushar K.|last3=Boddu|first3=Veera M.}}</ref>

FOX-7 is similar to the insensitive chemical compound [[TATB]], which is a [[benzene]] ring compound with three [[amino]] and three [[nitro group]]s.<ref>{{cite journal|doi=10.1016/j.tet.2005.05.010|title=The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7)|year=2005|last1=Hervé|first1=Grégoire|last2=Jacob|first2=Guy|last3=Latypov|first3=Nikolaj|journal=Tetrahedron|volume=61|issue=28|pages=6743}}</ref> FOX-7 has a two-carbon backbone rather than a [[benzene]] ring, but the [[amino]] and [[nitro compound|nitro]] groups have similar effects in both cases according to published reports on the sensitivity and chemical decay processes of FOX-7.<ref name="Anniyappan" /> FOX-7 is stoichiometrically identical (but structurally unrelated)<ref name="Lochert" /> to the explosives and propellants [[RDX]] and [[HMX]], and therefore produces the same quantity of gas per gram, a key determinant of performance.<ref name="Anniyappan">{{cite journal|doi=10.1016/j.jhazmat.2006.03.034|title=Synthesis, characterization and thermolysis of 1,1-diamino-2,2-dinitroethylene (FOX-7) and its salts|year=2006|last1=Anniyappan|first1=M.|last2=Talawar|first2=M.B.|last3=Gore|first3=G.M.|last4= Venugopalan|first4=S.|last5=Gandhe|first5=B.R.|journal=Journal of Hazardous Materials|volume=137|issue=2|pages=812–9|pmid=16701943}}</ref>

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.<ref name="Lochert">{{cite techreport |first=Lochert |last=Ian J. |title=FOX-7 - A New Insensitive Explosive |number=DSTO-TR-1238 |publisher=Defense Science & Technology Organization |publication-place=Fisherman's Bend, Victoria, Australia |date=November 2001|year=2001 |url=https://apps.dtic.mil/dtic/tr/fulltext/u2/a399359.pdf |access-date=2021-01-25 |archive-date=2021-01-25 |archive-url=https://web.archive.org/web/20210125141310/https://apps.dtic.mil/dtic/tr/fulltext/u2/a399359.pdf |url-status=live }}</ref> Its explosive properties appear extremely favorable; in addition to its insensitive properties, the detonation velocity of mixtures of 80% FOX-7 plus [[binder (material)|binders]] is as high as [[Composition B]], and nearly pure FOX-7 based [[plastic bonded explosive]]s are slightly superior to [[RDX]].<ref>{{Cite journal|last1=Latypov|first1=Nikolai V.|last2=Bergman|first2=Jan|last3=Langlet|first3=Abraham|last4=Wellmar|first4=Ulf|last5=Bemm |first5=Ulf|year=1998|title=Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene|journal=Tetrahedron|volume=54|issue=38 |pages=11525–11536|doi=10.1016/s0040-4020(98)00673-5}}</ref> FOX-7 has been calculated to have a [[detonation velocity]] of 8,870 m/s.<ref>[http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Karlsson-165.pdf Detonation and Sensitivity Properties of FOX-7 and Formulations Containing FOX-7] {{Webarchive|url=https://web.archive.org/web/20050522150513/http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Karlsson-165.pdf |date=2005-05-22 }}, Karlsson et al., 2002, accessed Aug 25, 2005</ref> Charges composed of [[Ethylene-vinyl acetate|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.<ref name="Lochert" />

FOX-7 is produced as of 2018 by EURENCO [[Bofors]] AB of Sweden,<ref name=":1">{{cite techreport|last1=Sleadd|first1=Bradley A.|last2=Boruta|first2=David T.|last3=Clubb|first3=Joseph W.|title=Development of a CONUS manufacturing capability for FOX-7|institution=National Defense Industrial Association|date=24 April 2018|year=2018|url=https://ndiastorage.blob.core.usgovcloudapi.net/ndia/2018/imem/20157_Sleadd_Presentation.pdf|access-date=25 January 2021|archive-date=25 January 2021|archive-url=https://web.archive.org/web/20210125141312/https://ndiastorage.blob.core.usgovcloudapi.net/ndia/2018/imem/20157_Sleadd_Presentation.pdf|url-status=live}}</ref> having been made in batches up to 7kg in 2001.<ref name=":2">{{cite conference|last1=Ostmark|first1=Henric|last2=Bergman|first2=Helena|last3=Bemm|first3=Ulf|last4=Goede|first4=Patrick|date=6 July 2001|title=Energetic Materials: Ignition, Combustion and Detonation|url=https://apps.dtic.mil/sti/citations/ADA396885|conference=32nd International Conference of ICT|publisher=Fraunhofer-Institut für Chemische Technologie|pages=26-1 - 26-21|archive-url= https://web.archive.org/web/20210125141313/https://apps.dtic.mil/sti/citations/ADA396885|archive-date=2021-01-25|place=Karlsruhe, Germany|book-title=2, 2-dinitro-ethene-1, 1-diamine(FOX-7)- Properties, analysis and scale-up|access-date=2021-01-25|url-status=live}}</ref> 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.<ref name="Lochert" /> 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.<ref>US Patent 6312538 - Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound</ref>

FOX-7 is an attractive subject for research and development due to its combination of insensitivity and power. FOX-7 performs similarly to [[RDX]], one of the most powerful explosives and propellants in use, unlike other insensitive high explosives under investigation, such as TATB, [[nitrotriazolone]], [[TEX (explosive)|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,<ref name="Anniyappan" /> including in Australia, India, the USA, and Sweden.<ref name=":0" /><ref name="Lochert" /><ref name=":1" /><ref name=":2" />

== References ==
{{reflist}}

== Further reading ==
*{{cite journal|doi=10.1021/jp010289m|title=Classical and Quantum-Mechanical Studies of Crystalline FOX-7 (1,1-Diamino-2,2-dinitroethylene)|year=2001|last1=Sorescu|first1=Dan C.|last2=Boatz|first2=Jerry A.|last3=Thompson|first3=Donald L.|journal=The Journal of Physical Chemistry A|volume=105|issue=20|pages=5010|bibcode=2001JPCA..105.5010S}}
*{{cite journal|doi=10.1021/ic052150m|title=Α- and β-FOX-7, Polymorphs of a High Energy Density Material, Studied by X-ray Single Crystal and Powder Investigations in the Temperature Range from 200 to 423 K|year=2006|last1=Evers|first1=Jürgen|last2=Klapötke|first2=Thomas M.|last3=Mayer|first3=Peter|last4=Oehlinger|first4=Gilbert|last5=Welch|first5=Jan|journal=Inorganic Chemistry|volume=45|issue=13|pages=4996–5007|pmid=16780321}}

[[Category:Explosive chemicals]]
[[Category:Amines]]
[[Category:Nitroethenes]]
[[Category:Swedish inventions]]

FOX-7 - Revision history

UpdateBot: robot: Update article (please report if you notice any mistake or error in this edit)

>Tec15: added Category:Swedish inventions using HotCat