The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7)

Hervé, Grégoire; Jacob, Guy; Latypov, Nikolaj V.

doi:10.1016/j.tet.2005.05.010

Cited by 95 publications

(49 citation statements)

References 11 publications

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“…[22] Compound 13 also acts as a synthon for a number of dinitromethylene compounds. [23] The condensation of 13 with glyoxal in aqueous KOH solution gives the heterocyclic 3-(dinitromethyl)-1, 2, 4-triazine potassium salt (14), [24] which proved to be a reactive substrate in a condensation reaction with 1-nitro-3-aminoguanidine, forming the corresponding derivative, 3-nitrimino-7-dinitromethylene-octahydro- [1,2,4] The syntheses of HEDMs which contain polynitro, azo, and heterobicyclic functional groups from FOX-7 were successful. The structures of these compounds were deter- Figure 1.…”

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confidence: 99%

The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials

Gao

Shreeve

2015

Angew Chem Int Ed

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New derivatives of 1,1-diamino-2, 2-dinitroethene (FOX-7) are reported. These highly oxygen- and nitrogen-rich compounds were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis (EA), and differential scanning calorimetry (DSC). X-ray structure determination of (E)-1,2-bis{(E)-2-chloro-1-(chloroimino)-2,2-dinitroethyl}diazene) (10), N1, N2-dichloro-1, 2-diazenedicarboximidamide (11), and (E,E)-N,N'-1,2-ethanediylidenebis(2, 2-dinitro-2-chloro-ethanamine) (12) was helpful in their characterization. Heats of formation (HOF) were calculated (Gaussian 03) and combined with experimental densities to estimate the detonation velocities (D) and pressures (P) of the high-energy-density materials (HEDMs) (EXPLO5, v6.01). The compounds exhibit good thermal stability, high density, positive HOF, acceptable oxygen balances, and excellent detonation properties, which often are superior to that of 1,3,5-trinitroperhydro-1,3,5-triazine (RDX).

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confidence: 99%

The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials

Gao

Shreeve

2015

Angew Chem Int Ed

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“…5,8,9 Methylamine was used as a kind of nucleophilic attack agent at the positive end of the carbon-carbon double bond, with subsequent replacement of an amino group by a methylamine group. However, once one of the two amino groups was substituted by the nucleophile, it was very difficult to replace the other one.…”

Section: Resultsmentioning

confidence: 99%

“…So, FOX-7 exists in manifold tautomers and resonances and can react with some nucleophiles to synthesize new high energy derivatives. 5,8,9 Our interest mainly consisted in modifying molecular structure of FOX-7 in order to obtain some new high energetic compounds and studying the structure-property relationship of the derivatives. We have prepared a series of derivatives of FOX-7, such as 1-amino-1-hydrazino-2,2-dinitroethene (AHDNE), 2-(di…”

Section: Introductionmentioning

confidence: 99%

Structural Characterization and Thermal Behavior of 1‐Amino‐1‐methylamino‐2,2‐dinitroethylene

Xu¹,

Wang

Ren

et al. 2010

Chin. J. Chem.

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A novel high energetic material, 1-amino-1-methylamino-2,2-dinitroethylene (AMFOX-7), was synthesized through 1,1-diamino-2,2-dinitroethylene (FOX-7) reacting with methylamine in N-methyl pyrrolidone (NMP) at 80.0 ℃, and its structure was determined by single crystal X-ray diffraction. The crystal is monoclinic, space group P2 1 /m with crystal parameters of a＝6.361(3) Å, b＝7.462(4) Å, c＝6.788(3) Å, β＝107.367 (9)

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“…2,3,5,[12][13][14][15] Our interest mainly consisted in modifying molecular structure of FOX-7 in order to obtain some new high-energy compounds and research their structure-property relationship.…”

Section: Introductionmentioning

confidence: 99%

Structural and Thermal Characteristics of a High-Nitrogen Energetic Material: G(AHDNE)

Lu¹,

Xu²,

Zhang³

et al. 2012

Bulletin of the Korean Chemical Society

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A high-nitrogen energetic salt, 1-amino-1-hydrazino-2,2-dinitroethylene guanidine salt [G(AHDNE)], was synthesized by reacting of 1-amino-1-hydrazino-2,2-dinitroethylene (AHDNE) and guanidine hydrochloride in sodium hydroxide aqueous solution. The theoretical investigation on G(AHDNE) was carried out by B3LYP/ 6-311+G* method. The thermal behaviors of G(AHDNE) were studied with DSC and TG-DTG methods, and the result presents an intense exothermic decomposition process. The enthalpy, apparent activation energy and pre-exponential constant of the process are −1060 J g , respectively. The critical temperature of thermal explosion of G(AHDNE) is 152.63 °C. The specific heat capacity of G(AHDNE) was studied with micro-DSC method and theoretical calculation method, and the molar heat capacity is 314.69 J mol −1 K −1 at 298.15 K. Adiabatic time-to-explosion of G(AHDNE) was calculated to be a certain value between 60-72 s. The detonation velocity and detonation pressure were also estimated. G(AHDNE) presents good performances.

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The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7)

Cited by 95 publications

References 11 publications

The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials

The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials

Structural Characterization and Thermal Behavior of 1‐Amino‐1‐methylamino‐2,2‐dinitroethylene

Structural and Thermal Characteristics of a High-Nitrogen Energetic Material: G(AHDNE)

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