505-71-5

Basic information

• Product Name: N,N'-dinitroethylenediamine
• Synonyms: N,N'-dinitroethylenediamine;Ethylenebis(nitroamine);Haleite;N,N'-Dinitroethane-1,2-diamine;N,N'-Dinitroethene-1,2-diamine;N-(2-nitramidoethyl)nitramide
• CAS NO: 505-71-5
• Molecular Formula: C₂H₆N₄O₄
• Molecular Weight: 150.09344
• EINECS: 208-018-2
• Mol File: 505-71-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 175.25°C
• Boiling Point: 271.6°C (rough estimate)
• Flash Point: 157°C
• Appearance: /
• Density: 1.8244 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: N,N'-dinitroethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-dinitroethylenediamine(505-71-5)
• EPA Substance Registry System: N,N'-dinitroethylenediamine(505-71-5)

Safety Data

• Hazardous Substances Data: 505-71-5(Hazardous Substances Data)

Usage

General Description

N,N'-dinitroethylenediamine, also known as FOX-7, is a powerful high-energy explosive compound. It is used in military and defense applications due to its high stability, insensitivity to shock, and high thermal stability. This chemical is commonly used in the production of propellants, explosives, and pyrotechnic compositions due to its superior mechanical and thermal properties. FOX-7 has a higher heat of formation and a larger oxygen balance than conventional explosives, making it ideal for use in advanced munitions and ordnance. However, the synthesis and handling of N,N'-dinitroethylenediamine require specialized expertise and caution due to its high reactivity and potential hazards.

Upstream product

• 2536-18-7 1,3-dinitroimidazolidin-2-one 
• 7732-18-5 water 
• 10120-27-1 N-hydroxymethylethylenedinitroamine 
• 120-93-4 imidazolidone 
• 3082-46-0 N,N'-dinitro-N,N'-ethanediyl-bis-carbamic acid dimethyl ester 
• 7664-41-7 ammonia 
• 2639-89-6 N,N'-dinitro-N,N'-ethane-1,2-diylbis(carbamic acid) diethyl ester 
• 28236-80-8 N,N'-dichloro-N,N'-dinitro-ethylenediamine 
• 58851-62-0 tetra-N-chloro-ethylenediamine 
• 7697-37-2 nitric acid 
• 56-23-5 tetrachloromethane 
• 5755-26-0 N-acetoxymethyl-N'-[(acetoxymethyl-nitro-amino)-methyl]-N,N'-dinitro-ethylenediamine 
• 5754-91-6 1,3-dinitro-1,3-diazacyclopentane 
• 41404-99-3 N,N'-divinyl-N,N'-dinitroethylenediamine 

Downstream Products

• 14168-48-0 2,5-dinitro-2,5-diaza-1,6-hexanediyl diacetate 
• 10308-90-4 N-methyl-N,N'-dinitroethylenediamine 
• 4164-34-5 2,5-dinitro-2,5-diazahexane 
• 28236-80-8 N,N'-dichloro-N,N'-dinitro-ethylenediamine 
• 107-21-1 ethylene glycol 
• 7732-18-5 water 
• 75-07-0 acetaldehyde 

Relevant articles and documents

Crystal Engineering of Energetic Materials: Co-crystals of Ethylenedinitramine (EDNA) with Modified Performance and Improved Chemical Stability

In the area of energetic materials, co-crystallization is emerging as a new technology for modifying or enhancing the properties of existing energetic substances. Ethylenedinitramine (EDNA) is a known energetic material which requires attention partly due to its chemical instability originating with its two highly acidic protons. In order to stabilize EDNA, a co-crystallization approach targeting the acidic protons using a series of co-crystallizing agents with suitable hydrogen-bond acceptors was employed. Fifteen attempted co-crystallizations resulted in eight successful outcomes and six of these were crystallographically characterized and all showed evidence of hydrogen bonds to the intended protons. Calculated detonation properties and experimental thermal and impact data for the co-crystals were obtained and compared with those of pure EDNA. The co-crystal of EDNA and 1,2-bis(4-pyridyl)ethylene was recognized as a more thermally stable alternative to EDNA while the co-crystal of EDNA and pyrazine N,N′-dioxide showed comparable detonation strengths (and much improved chemical stability) compared with that of EDNA. The co-crystals EDNA:4,4′-bipyridine and EDNA:pyrazine N,N′-dioxide were found to be about 50 % less impact sensitive than EDNA, all of which illustrate how co-crystallizations can be utilized for successfully modifying specific aspects of energetic materials. The taming of EDNA: Ethylenedinitramine (EDNA) is a known energetic material the chemical instability of which originates with its two highly acidic protons. Co-crystallizations of EDNA demonstrate that the acidic protons can be targeted with suitable hydrogen-bond acceptors, which improves chemical stability and offers an avenue for modulating thermal properties, impact sensitivity, and overall performance of the material (see picture).

Energetic propane-1,3-diaminium and butane-1,4-diaminium salts of N,N′-dinitroethylenediazanide: syntheses, crystal structures and thermal properties

The acidity of the amine H atoms and the consequent salt formation ability of ethylenedinitramine (EDNA) were analyzed in an attempt to improve the thermal stability of EDNA. Two short-chain alkanediamine bases, namely propane-1,3-diamine and butane-1,4-diamine, were chosen for this purpose. The resulting salts, namely propane-1,3-diaminium N,N′-dinitroethylenediazanide, C3H12N22+·C2H4N4O42?, and butane-1,4-diaminium N,N′-dinitroethylenediazanide, C4H14N22+·C2H4N4O42?, crystallize in the orthorhombic space group Pbca and the monoclinic space group P21/n, respectively. The resulting salts display extensive hydrogen-bonding networks because of the presence of ammonium and diazenide ions in the crystal lattice. This results in an enhanced thermal stability and raises the thermal decomposition temperatures to 202 and 221 °C compared to 180 °C for EDNA. The extensive hydrogen bonding present also plays a crucial role in lowering the sensitivity to impact of these energetic salts.

Process for the synthesis and recovery of nitramines

A method is provided for the synthesis of nitramines, and the recovery of the nitramines from a clathrate.