5128-28-9

Usage

Uses

Used in Military Applications:
4,6-Dinitrobenzofuroxane is used as a high-energy density material for the development of explosives and propellants due to its high reactivity and energy release upon detonation. Its use in this industry is for enhancing the power and efficiency of military ordnance while ensuring that safety protocols are strictly adhered to.
Used in Industrial Applications:
In the industrial sector, 4,6-dinitrobenzofuroxane serves as a component in the formulation of certain types of explosives and propellants that are utilized in mining, construction, and other heavy industries. It is used for its ability to provide a significant energy release, which is crucial for various industrial processes that require powerful explosive effects.

InChI:InChI=1/C6H2N4O6/c11-8(12)3-1-4(9(13)14)6-5(2-3)10(15)16-7-6/h1-2H

Upstream product

• 88-88-0 2,4,6-trinitrochlorobenzene 
• 480-96-6 benzofurazan oxide 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 5128-28-9 4,6-dinitrobenzofuroxan 
• 1600-31-3 2-azido-1,3,5-trinitro-benzene 
• 3698-53-1 1,2,3,5-tetranitrobenzene 
• 3702-88-3 5-nitrobenzofuroxane 
• 21416-60-4 naphthalene; compound with 2-chloro-1,3,5-trinitro-benzene 

Downstream Products

• 91949-42-7 4-(2-Methyl-benzofuran-3-yl)-5-nitro-7-aci-nitro-4,7-dihydro-benzo[1,2,5]oxadiazole 3-oxide 
• 91948-45-7 C₇H₅N₄O₇^(1-) 
• 91948-45-7 potassium 4-methoxy-5,7-dinitro-4,5-dihydrobenzofurazanide 3-oxide 

Relevant academic research and scientific papers

Oxidation of Cobalt(II) Tetrapyrroles in the Presence of an Electron Acceptor

The interaction of cobalt(II) porphyrins and chlorin with 4,6-dinitrobenzofurazan 1-oxide (dnbfo) has been studied by spectroscopic methods.Initially all the cobalt(II) porphyrins form molecular complexes with the electron acceptor dnbfo, but with time a complete electron transfer is observed.This results in the formation of cobalt(III) porphyrins and the anion radical of dnbfo.The electron transfer is facilitated in the presence of molecular oxygen.The rate of oxidation is dependent on the porphyrin ring substituents as well as on the solvent mixture used.In the case of cobalt(II) 5,10,15,20-tetraphenylchlorin first oxidation occurs to cobalt(II) 5,10,15,20-tetraphenylporphyrin and this is followed by metal oxidation to give the cobalt(III) porphyrin.The oxidation of the cobalt(II) porphyrins and formation of the anion radical of dnbfo has been monitored by ESR spectroscopy.The g value and the linewidth of the radical compares well with that of the anion formed by chemical reduction.Proton and 19F NMR data confirm the occurrence of the electron-transfer reaction.

Thermal behavior, decomposition mechanism and thermal safety of 5,7-diamino-4,6-dinitrobenzenfuroxan (CL-14)

Thermal decomposition kinetics and mechanism of the high-energetic material 5,7-diamino-4,6-dinitrobenzenfuroxan (CL-14) were determined by differential scanning calorimetry (DSC), rapid scanning Fourier transform infrared spectroscopy, and simultaneous thermogravimetric and DSC analyses, coupled with FT-IR and mass spectroscopy. To evaluate the thermal safety of 5,7-diamino-4,6-dinitrobenzenfuroxan (CL-14), its specific heat capacity (Cp) was measured by DSC, and thermal conductivity (λ) was estimated. Kinetic parameters and heat of exothermic decomposition reaction of CL-14 were obtained by analysis of DSC curves. Kinetic parameters used to evaluate the thermal safety of CL-14, such as self-accelerating decomposition temperature (TSADT), critical temperature of thermal explosion (Tb) and impact sensitivity (H50), were obtained. Results showed that for CL-14, TSADT?=?282.0?°C and Tb?=?307.9?°C, whereas H50?=?39.79?cm, revealing that CL-14 had better thermal safety and heat resistance than HMX, RDX and GNTO.

Synthesis of condensed nitrofuroxanes using hydroxylamine

The possibility of preparing condensed nitrofuroxanes using hydroxylamine was examined.

The reactions of 4,6-dinitrobenzofuroxan with sulfite ions in water; cis-trans isomerism in the 1:2 adducts

The reaction of 4,6-dinitrobenzofuroxan with sulfite ions in water results in the formation of a 1:1 adduct with high thermodynamic stability, K1 1.3 × 1013 dm3 mol-1, and in a 1:2 adduct which may exist in trans- and cis-isomeric forms.

Interaction of nitroalkane anions with superectrophilic 4,6-dinitrobenzofuroxan: ?-adduct formation and vicarious heteroaromatic substitution of hydrogen.

Carbanions of nitromethane, nitroethane, 1-nitropropane and 2-nitropropane readily add to 4,6-dinitrobenzofuroxan (DNBF) to form carbon-bonded ?-adducts (5a-d) which are very stable and isolable as crystalline alkali salts.In the case of the nitroethane and 1-nitropropane systems, the complexation results in the formation of two chiral centres, so that diastereoisomeric ?-adducts are formed.Structural features are discussed on the basis of the collected 1H and 13C NMR parameters.Contary to expectation, addition of base (MeO-, CF3CH2O-, NEt3) to dimethyl sulfoxide sol utions of 5a-c did not result in further ionization of the nitroalkane moiety and formation of dianions 7a-c.Instead, it promotes a base-catalysed β-elimination of nitrous acid.This process also occurs and is especially clean with the 2-nitropropane aduct 5d, an example of the rare occurrence of a nucleophilic aromatic substitution of an hydrogen atom assisted by the departure of a vicarious nitro group in the exocyclic moiety.The result is re-aromatization of the carboxylic ring of 5a-d with formation of carbanions (8a-d) which are the conjugate bases of the corresponding 7-R-4,6-dinitrobenzofuroxans (R=Me, Et, Prn, Pri).Despite their lack of stability, NMR characterization of these carbanions could be made.Rate and equilibrium data for DNBF complexation by the four nitroalkane anions studied have been obtained in aqueous solution.The result how that the thermodynamic stability ofthe adducts 5a-d is 105-108 times greater than that of the analogous ?-adducts of 1,3,5-trinitrobenzene, the common reference aromatic electrophile in ?-complexation processes.Such stability differences emphasize the estremely high electrophilic character of DNBF.Analysis of the rate data reveals that nitrocarbanions exhibit especially low intrinsic reactivities in ?-adduct forming reactions.

AMBIPHILIC FUROXAN RING. BENZOFUROXAN OXIDATION BY PERACID AND REDUCTION BY COPPER

Monopersulfuric acid, trifluoroperacetic acid and hydrogen peroxide in polyphosphonic acid, or with selenium dioxide in t-butyl alcohol, or in tetramethylene sulfone have each oxidized benzofuroxan into o-dinitrobenzene.Monopersulfuric acid oxidized 4-nitrobenzofuroxan into 1,2,3-trinitrobenzene (80percent) and 4,6-dinitrobenzofuroxan into 1,2,3,5-tetranitrobenzene (99percent); hydrogen peroxide in polyphosphoric acid was moderately efficient for the latter oxidation.Copper in acidified ethanol transformed 4,6-dinitrobenzofuroxan into picramide quantitatively.