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7, 8-dinitropyrazole[1, 5-a][1, 3, 5]triazine-2, 4-diamine and preparation method thereof

A technology of dinitropyrazole and nitropyrazole, applied in the fields of nitrated acyclic/alicyclic/heterocyclic amine explosive composition, organic chemistry, etc., which can solve the problems of increased sensitivity and reduced thermal stability

Inactive Publication Date: 2021-05-28
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Energetic materials are the power source and damage source for weapons to strike targets, and their energy levels directly affect the performance of weapon systems. However, when the energy of energetic materials is increased, their sensitivity will often increase and their thermal stability will decrease.

Method used

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  • 7, 8-dinitropyrazole[1, 5-a][1, 3, 5]triazine-2, 4-diamine and preparation method thereof
  • 7, 8-dinitropyrazole[1, 5-a][1, 3, 5]triazine-2, 4-diamine and preparation method thereof
  • 7, 8-dinitropyrazole[1, 5-a][1, 3, 5]triazine-2, 4-diamine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 3,5-Diamino-4-nitropyrazole (3mmol, 0.429g) was dispersed in 5ml of methanol, and 5% dilute hydrochloric acid (10ml) was added to the above solution, stirred for 10 minutes, and suction filtered to obtain 3, 5-Diamino-4-nitropyrazole hydrochloride. The hydrochloride and dicyandiamide (4mmol, 0.33g) were added to 15ml of methanol, reacted at 40°C for 24 hours, cooled, filtered with suction, and recrystallized with water to obtain intermediate 1 (yield: 50%).

[0027] Under an ice-water bath, Intermediate 1 (3mmol, 0.63g) was added in batches to 10ml of concentrated sulfuric acid, and then 5ml of 20% hydrogen peroxide aqueous solution was added to react at room temperature for 5 hours. The reaction solution was poured into ice water and washed with ethyl acetate. After extraction, drying and spin-off of the solvent, the compound 7,8-dinitropyrazol[1,5-a][1,3,5]triazine-2,4-diamine was obtained (yield: 41%). H NMR spectrum δ: 8.81(s, 1H, NH 2 ), 8.56(s, 1H, NH 2 ), 8.04...

Embodiment 2

[0029] 3,5-diamino-4-nitropyrazole (3mmol, 0.429g) was dispersed in 8ml of ethanol, and 30% hydrochloric acid (2ml) was added to the above solution, stirred for 20 minutes, and suction filtered to obtain 3,5 - Diamino-4-nitropyrazole hydrochloride. The hydrochloride and dicyandiamide (4mmol, 0.33g) were added to 15ml of methanol, reacted at 50°C for 24 hours, cooled, filtered with suction, and recrystallized with water to obtain intermediate 1 (yield: 60%).

[0030] Under an ice-water bath, Intermediate 1 (3mmol, 0.63g) was added in batches to 10ml of trifluoroacetic acid, then 5ml of 30% hydrogen peroxide aqueous solution was added, and reacted at room temperature for 8 hours. The reaction solution was poured into ice water and extracted with chloroform. , dried and spin-off the solvent to obtain the compound 7,8-dinitropyrazol[1,5-a][1,3,5]triazine-2,4-diamine (yield: 30%). H NMR spectrum δ: 8.81(s, 1H, NH 2 ), 8.56(s, 1H, NH 2 ), 8.04(s, 1H, NH 2 ), 7.77 (s, 1H, NH 2 )...

Embodiment 3

[0032] 3,5-diamino-4-nitropyrazole (3mmol, 0.429g) was dispersed in 5ml of methanol, and concentrated sulfuric acid (2ml) with a concentration of 98% was added to the above solution, stirred for 10 minutes, and suction filtered to obtain 3, 5-Diamino-4-nitropyrazole sulfate. Add the sulfate and dicyandiamide (4mmol, 0.33g) into 30ml ethanol, react at 70°C for 8 hours, cool, filter with suction, and recrystallize with water to obtain intermediate 1 (yield: 52%).

[0033] Under an ice-water bath, intermediate 1 (3 mmol, 0.63 g) was added in batches to 6 ml of trifluoroacetic acid, and then 2.5 ml of 50% hydrogen peroxide aqueous solution was added to react at room temperature for 12 hours. The reaction solution was poured into ice water and washed with two Extract with methyl chloride, dry, and spin off the solvent to obtain compound 7,8-dinitropyrazol[1,5-a][1,3,5]triazine-2,4-diamine (yield: 20%) . H NMR spectrum δ: 8.81(s, 1H, NH 2 ), 8.56(s, 1H, NH 2 ), 8.04(s, 1H, NH 2...

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Abstract

The invention discloses 7, 8-dinitropyrazol [1, 5-a][1, 3, 5]triazine-2, 4-diamine and a preparation method thereof. The compound has a structural formula as descried in the specification. The energetic compound 7, 8-dinitropyrazol[1, 5-a][1, 3, 5]triazine-2, 4-diamine has the characteristics of high energy, low sensitivity, good thermal stability and the like, and is an energetic material with potential application value.

Description

technical field [0001] The invention relates to the technical field of energetic materials, in particular to an energetic compound 7,8-dinitropyrazol[1,5-a][1,3,5]triazine-2,4-diamine and a preparation method thereof . Background technique [0002] Energetic materials are the power source and damage source for weapons to strike targets, and their energy levels directly affect the performance of weapon systems. However, when the energy of energetic materials is increased, their sensitivity will often increase and their thermal stability will decrease. The development of energetic compounds with high energy, low sensitivity and good thermal stability has always been a research hotspot in the field of energetic materials and is full of challenges. So far, the energetic compounds with the above characteristics are relatively limited, typically triaminotrinitrobenzene (TATB), 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM- 105) etc. Therefore, it is of great significance to deve...

Claims

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Application Information

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IPC IPC(8): C07D487/04C06B25/34
CPCC07D487/04C06B25/34
Inventor 王毅张庆华宋思维
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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