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4-cyano-5-nitro-1, 2, 3-triazole metal salt as well as preparation method and application thereof

A technology of metal salt and dinitropyrazole, applied in the field of energetic materials, can solve problems such as poor safety

Pending Publication Date: 2022-06-03
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is the defect that existing high nitrogen-containing energetic compounds are relatively poor in safety. For this reason, the present invention provides 4-cyano-5-nitro-1,2,3-triazole metal salts, its Preparation method and application

Method used

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  • 4-cyano-5-nitro-1, 2, 3-triazole metal salt as well as preparation method and application thereof
  • 4-cyano-5-nitro-1, 2, 3-triazole metal salt as well as preparation method and application thereof
  • 4-cyano-5-nitro-1, 2, 3-triazole metal salt as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Sodium dichloroisocyanurate (SDIC, 255 mg, 1.16 mmol, 1.5 eq) was dissolved in water (3 mL) at room temperature. Under stirring, 0.35 mL of acetic acid (6.19 mmol, 8.0 eq) was added dropwise thereto, and the mixture was stirred for 0.5 h for use. 1,4-Diamino-3,5-dinitropyrazole (DADNP, 145 mg, 0.77 mmol) was dissolved in 8 mL of acetonitrile, cooled to -5°C, and SDIC / acetic acid aqueous solution was added dropwise while stirring, and the addition was completed in 0.5 h. After the DADNP is consumed, add sodium carbonate to the reaction solution to a pH value greater than 7, and concentrate to obtain a crude product. Column chromatography was performed using silica gel, followed by pure petroleum ether, petroleum ether:ethyl acetate=10:1, then 5:1, 1:1, 1:2 and pure ethyl acetate to obtain pure product, and 94 mg of yellow White powdery solid, yield 57%. 13 CNMR (100MHz, DMSO-d 6 , ppm) δ: 155.73, 114.81, 113.83; IR (cm -1): 3432, 2927, 2856, 2465, 2262, 1545, 1504, 1...

Embodiment 2

[0046] Sodium dichloroisocyanurate (SDIC, 170 mg, 0.77 mmol, 1.0 eq) was dissolved in water (3 mL) at room temperature. Under stirring, 0.35 mL of acetic acid (6.19 mmol, 8.0 eq) was added dropwise thereto, and the mixture was stirred for 0.5 h for use. 1,4-Diamino-3,5-dinitropyrazole (DADNP, 145 mg, 0.77 mmol) was dissolved in 8 mL of acetonitrile, cooled to 0° C., and SDIC / acetic acid aqueous solution was added dropwise while stirring. After the DADNP is consumed, add sodium carbonate to the reaction solution to a pH value greater than 7, and concentrate to obtain a crude product. Use silica gel for column chromatography, followed by pure petroleum ether, petroleum ether: ethyl acetate = 10:1 to 5:1 and 1:1, 1:2 and pure ethyl acetate to obtain pure product, to obtain 86 mg of yellow White powdery solid, yield 52%.

Embodiment 3

[0048] Sodium dichloroisocyanurate (SDIC, 170 mg, 0.77 mmol, 1.0 eq) was dissolved in water (3 mL) at room temperature. Under stirring, 0.35 mL of acetic acid (6.19 mmol, 8.0 eq) was added dropwise thereto, and the mixture was stirred for 0.5 h for use. 1,4-Diamino-3,5-dinitropyrazole (DADNP, 145 mg, 0.77 mmol) was dissolved in 8 mL of acetonitrile, cooled to 5° C., and SDIC / acetic acid aqueous solution was added dropwise while stirring. After the DADNP is consumed, add sodium bicarbonate to the reaction solution to a pH value greater than 7, and concentrate to obtain a crude product. Use silica gel for column chromatography, followed by pure petroleum ether, petroleum ether: ethyl acetate = 10:1, then 5:1 and 1:1, 1:2 and pure ethyl acetate to obtain pure product, and 89 mg of yellow White powdery solid, yield 54%.

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Abstract

The invention discloses a 4-cyano-5-nitro-1, 2, 3-triazole metal salt as well as a preparation method and an application of the 4-cyano-5-nitro-1, 2, 3-triazole metal salt. The invention discloses a 4-cyano-5-nitro-1, 2, 3-triazole metal salt as shown in a formula I in the specification, and a preparation method of the 4-cyano-5-nitro-1, 2, 3-triazole metal salt. The invention discloses a preparation method of 4-cyano-5-nitro-1, 2, 3-triazole metal salt, which comprises the following steps: dissolving 1, 4-diamino-3, 5-dinitropyrazole (DADNP) as shown in a formula II in a solvent, adding an acidified or unacidified reagent A to react, and adding a pH regulator to regulate the pH value to be greater than 7 after the reaction is finished, thereby obtaining the 4-cyano-5-nitro-1, 2, 3-triazole metal salt. The compound belongs to the field of energetic materials and can be applied to energetic materials.

Description

technical field [0001] The invention belongs to the field of energetic materials, in particular to 4-cyano-5-nitro-1,2,3-triazole metal salt, a preparation method and application thereof. Background technique [0002] High-nitrogen energetic compounds have attracted great attention in the design and synthesis of energetic materials due to their high nitrogen content and clean decomposition products. Among them, the 1,2,3-triazole ring contains three adjacent nitrogen atoms, which makes it have a higher enthalpy of formation, and two carbon atoms can be connected to energetic groups for energetic derivatization. Therefore, 1 The ,2,3-triazole ring is very suitable for use as the heterocyclic skeleton of high nitrogen energetic compounds. The introduction of nitro groups on 1,2,3-triazole can improve the oxygen balance of the compound and increase its energy level. [0003] The impact sensitivity of 2,2',4,4',6,6'-hexanitrostilbene (HNS) of the currently used heat-resistant e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04C06B41/00
CPCC07D249/04C06B41/00
Inventor 杨军黄海丰李光磊
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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