3, 3-diamno-4 ,4-azoxyfurazan (DAAzF)

 Explosive characteristics: Velocity of detonation (at a density of 1.69 g/cc) 8000 m / sec. Pressure of the explosion about 299 kbar at a density of 1.69 g / cm.

Physical properties: О ранжево-желтые кристаллы. About Ranjeva yellow crystals. Практическая плотность 1,69 г/см. Practical density of 1.69 g / cm. Температура начала разложения 248С. The temperature of the beginning of the expansion 248S.

Synthesis: A 500ml flask was poured into 100 grams of 30% hydrogen peroxide at 18C and added in 10 minutes 55 grams 98% sulfuric acid with active stirring. Далее в смесь вносят 10 грамм 3,4-диаминофуразана и активно перемешивают в течении 24 часов. Next, the mixture is made by 10 grams of 3,4-diaminofurazana and actively stirred for 24 hours. DAAF выпадает в виде оранжевых кристаллов, которые отфильтровывают и промывают водой. DAAF falls in the form of orange crystals which are filtered and washed with water. Грязный DAAF растворяют в 22 мл ДМСО который затем разбавляют 45 мл воды и отфильтровывают чистый DAAF. Dirty DAAF dissolved in 22 ml DMSO, which is then diluted with 45 ml water and filtered clean DAAF.

This compound is a precursor for is for the synthesis of DAA Z F.

Orange-yellow crystals. Insoluble in water. Thermally stable up to 248 ° C.  Almost insensitive to the impact (more than 320 cm for a 2.5 kg load), friction and static electricity. Critical diameter of detonation of 3mm.  Detonation velocity and pressure at the front of the detonation wave acc.  8020m / sec at 1.69 g/cm3 and 29.9 GPa. Heat of formation of 106 kcal / mol.  A good press Density of 1,747 g/cm3.  Prepared by oxidation of 3,4-diaminofurazan by hydrogen peroxide and 88%. sulfuric acid, with a yield of 88%. A potential low cost production insensitive explosive.
Known also similar to the properties of 3,3 '-diamino-4, 4'-azofurazan DAAzF H 2 N (C 2 N 2 O)-N = N-(C 2 N 2 O) NH 2 - dark orange crystals are almost insensitive to shock (over 320 cm for a 2.5 kg load), friction and static electricity.  In terms of thermal stability it is close to Hexanitrostilbene. Detonation velocity and pressure at the front of the detonation wave accelleration 7600m / sec at 1.65 g/cm3 and 26.2 GPa.  A good press Density of 1.72 g/cm3. For the synthesis of 
3,3 '-diamino-4,4'-azoxy furazan to 3,3'-diamino-4,4'-azofurazan, zinc dust in a mixture of glacial acetic acid and methanol. 3,3 '-diamino-4, 4'-azofurazan then oxidized to DAAzF. The total yield of DAAF approximately 92%. A potentially heat-resistant insensitive explosive.
Some derivatives furazano and furoxan are of considerable interest as components of high explosives and propellants. It is usually fairly stable liquid or solid yellow or colorless. High-density. good resistance to impact..
Dinitrofurazanovy ether [(O 2 N) C 2 N 2 O] 2 O t pl. 62°С. 62 ° C.  Density of 1,907 g/cm3.  Heat of formation of 73 kcal / mol. Detonation velocity of 9.2 m / c at 1.9g/cm3.  Can be obtained by heating 3,4-dinitrofurazan in acetonitrile in the presence of carbonate.
Dinitroazoxyfurazan (O 2 N) (C 2 N 2 O) N (O) = N (C 2 N 2 O) (NO 2) t pl. 112°С. 112 ° C. t разл ок 206°С.  decomposition temperature: roughly 206 ° C. Density of 1.82 g/cm3. Heat of formation of 155 kcal / mol.  Detonation velocity of 9.02 m / sec at 1.78g/cm3. Can be obtained by oxidation of 3,4-diaminofurazan.
4,4 '-dinitro-3, 3'difurazan [(O 2 N) C 2 N 2 O] 2     t pl. 85°С.  Thermally stable up to 250 ° C. Sensitive to impact, friction and fire. Sensitivity to shock is roughly
12 cm. Heat of formation of 101 kcal / mol. Calculated detonation velocity 8650 m / sec at 1.8 g/cm3. Density 1.85g/sm3. Can be obtained by oxidation of 4,4 '-diamino-3,3'-difurazan mixture of concentrated hydrogen peroxide and trifluoroacetic acid.


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dinitrofurazan C 2 N 4 O 5 ,  molar weight 160,05, melting point (minus) -15 ° С,  density 1.62 g/см 3

heat of formation 55kcal/mol

detonation velocity 7.98 km/sec


F_15.gif (1231 bytes)  diaminofurazan C2N4H4O density: 1.61 g/cm3


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azenonitrofurazan O2N(C2N2O)N=N(C2N2O)NO2     melting point: 56degC.



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azoxynitrofurazan  molar weight: 272.09, melting point 112degC, heat of formation: 155kcal/mol,
calculated density 1.82g/cm3
detonation velocity: 9.02 km/sec (at a density of 1.72g/cm3)

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C4N8O4 molar weight 224, melting point 35 degC, heat of formation 201 kcal/mol

density: 1.91 g/cm3,

detonation velocity: 9.16 km/sec (at a density of 1.84g/cm3)

1,2,3-Triazole ideas

Apparently nitroacetone can be used to make nitrogenous rings, supporting my idea that nitroacetone should be able to condense with sodium azide to form

"One-pot synthesis of 5-nitropyridines by the cyclocondensation of nitroacetone, triethyl orthoformate and enamine"

Galina P. Sagitullina, Anna K. Garkushenko,  Evgeny G. Atavin, and Reva S. Sagitullin

Department of Organic Chemistry, F. M. Dostoevsky Omsk State University, 644077 Omsk, Russian Federation

Could one not condense CH2O and excess nitromethane (using the nitroaldol condensation reaction, simply heat with NaOH) to make nitroethanol (which is poisonous and easily absorbs through skin). Then oxidize nitroethanol with a selective oxidizer such as 2-Iodoxybenzoic acid (no water can be present or the nitro group will disproportionate off from the acidity in a Meyer reaction) or pyridinium chlorochromate. This would then form 2-nitroacetaldehyde O2NCH2CH=O.
This could then potentially cyclize with sodium azide to form plain 4-nitro-1,2,3-triazole, without the methyl group that would have resulted if nitroacetone had been used. Possibly heating in concentrated nitric acid (100degC) could simultaneously oxidize the methyl group to a carboxyl, then decarboxylate the molecule, and finally add a nitro group in. While plain 1,2,3-triazole cannot be directly nitrated, 4-nitro-1,2,3-triazole is more susceptible.

At least for benzoic acid, decarboxylation proceeds readily by heating (only 100degC) if there is another electron withdrawing group (such as a chlorine atom) on the ring. (this would result in chlorobenzene and carbon dioxide).

Some information about 2-Iodoxybenzoic acid: it can oxidize methanol to formaldehyde in 94% yield, and can similarly oxidize ethylene glycol (vehicle anti-freeze) to glyoxal. However, dimethyl sulfoxide (DMSO) can not be used as a solvent for the latter, as its pressence will cause the ethylene glycol to be oxidized to formaldehyde instead. The 2-Iodoxybenzoic acid can then be re-oxidized and recycled after completion of the reaction.
2-Iodoxybenzoic acid can be prepared by the slow addition, over a half hour, of potassium bromate (76.0 g, 0.45 mol) to a vigorously stirred sulfuric acid mixture (0.73 M, 730 mL) containing 2-iodobenzoic acid (85.2 g, 0.34 mol).

Here is the nitroaldol condensation procedure between nitroethane and CH2O. A lesser ammount of nitromethane could very easily substitute for the nitroethane:
75.1g Nitroethane, 0.3g calcium hydroxide and 80g 40% formaldehyde solution was dissolved in 75ml ethanol with stirring and was allowed to stand for 48h at room temperature. Distillation at 100-105°C/13 mmHg (85-86°C/6 mmHg, 99°C/10 mmHg) gave 48g 2-nitropropanol (46%) and 14.3g of 2-nitro-2-methyl- 1,3-propanediol, the latter remained as a crystalline residue in the distillation flask after distillation of the 2-nitropropanol.

Anders Hoveland,
Mar 17, 2011, 12:05 PM