53817-16-6

Basic information

• Product Name: 1H-1,2,3-triazole-4,5-dicarbonitrile
• Synonyms: 1H-1,2,3-triazole-4,5-dicarbonitrile;Einecs 258-800-2;1H-1,2,3-triazole-4,5-dicarbonitrile（WS200398）
• CAS NO: 53817-16-6
• Molecular Formula: C₄HN₅
• Molecular Weight: 119.08424
• EINECS: 258-800-2
• Mol File: 53817-16-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 145 °C
• Boiling Point: 523°Cat760mmHg
• Flash Point: 160.5°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 4.93E-11mmHg at 25°C
• Refractive Index: 1.589
• PKA: 2.56±0.70(Predicted)
• CAS DataBase Reference: 1H-1,2,3-triazole-4,5-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,3-triazole-4,5-dicarbonitrile(53817-16-6)
• EPA Substance Registry System: 1H-1,2,3-triazole-4,5-dicarbonitrile(53817-16-6)

Safety Data

• Hazardous Substances Data: 53817-16-6(Hazardous Substances Data)

Usage

General Description

1H-1,2,3-Triazole-4,5-dicarbonitrile, also known as triazole dicarbonitrile, is a chemical compound with the molecular formula C4HN5. It is a white, crystalline powder that is primarily used in the field of medicinal chemistry and pharmaceuticals as a building block for the synthesis of various biologically active compounds. 1H-1,2,3-Triazole-4,5-dicarbonitrile has attracted attention due to its pharmacological properties and potential therapeutic applications, particularly in the areas of anti-cancer, antifungal, and antibacterial agents. Its unique molecular structure and functional groups make it a versatile intermediate for producing various pharmaceuticals and agrochemicals. Additionally, it has garnered interest in academic research for its potential as a scaffold for drug design and discovery.

InChI:InChI=1/C4HN5/c5-1-3-4(2-6)8-9-7-3/h(H,7,8,9)

Upstream product

• 1187-42-4 diaminomaleonitrile 
• 18514-52-8 2,3-diaminomaleonitrile 
• 1187-12-8 1,1-diamino-2,2-dicyanoethylene 

Downstream Products

• 957124-53-7 N₄,N₅-diphenyl-2H-1,2,3-triazole-4,5-dicarbohydrazonamide 
• 57613-19-1 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide 
• 4546-95-6 1H-1,2,3-triazole-4,5-dicarboxylic acid 

Relevant articles and documents

The nitrogen-rich energetic compound 4-carboxamide-5-(1: H -tetrazol-5-yl)-1 H -1,2,3-triazole and its 1D sodium complex: Synthesis and properties

The new nitrogen-rich energetic compound 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole (2) and its sodium complex (3) have been synthesized using diaminomaleodinitrile as the starting material in a three step synthesis. Both of the compounds were comprehensively characterized using Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS) and elemental analysis (EA). The sodium complex of 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole was confirmed using single-crystal X-ray diffraction for the first time. The thermal stability of the two compounds has been measured using differential scanning calorimetry (DSC), which indicated that the decomposition peak temperatures were 332.6 °C (2) and 374.1 °C (3). The density and enthalpy of formation of 2 were calculated with Gaussian 09 and the detonation pressure (21.9 GPa) and the detonation velocity (7182 m s-1) were predicted by Kamlet-Jacobs equations. Compound 2 was not sensitive to impact (>40 J) or friction (>360 N).

Gem-dinitromethyl-substituted Energetic Metal–Organic Framework based on 1,2,3-Triazole from in situ Controllable Synthesis

Synthesizing energetic metal–organic frameworks at ambient temperature and pressure has been always a challenge in the research area of energetic materials. In this work, through in situ controllable synthesis, energetic metal–organic framework gem-dinitromethyl-substituted dipotassium 4,5-bis(dinitromethyl)-1,2,3-triazole with a “cage-like” crystal packing was obtained and characterized. Most importantly, for the first time, we found that it could be successfully afforded with a catalytic effect of trifluoroacetic acid. This new compound exhibited its high density (2.04 g cm?3) at ambient temperature, superior detonation velocity (8715 m s?1) to that of lead azide (5877 m s?1) and comparable to that of RDX (8748 m s?1). Its detonation products are mainly N2 (48.1 %), suggesting it is also a green energetic material. The above-mentioned performance indicates its potential applications in detonator devices as lead-free primary explosive.

Combining the Advantages of Tetrazoles and 1,2,3-Triazoles: 4,5-Bis(tetrazol-5-yl)-1,2,3-triazole, 4,5-Bis(1-hydroxytetrazol-5-yl)-1,2,3-triazole, and their Energetic Derivatives

In the development of new energetic materials, the main challenge is the combination of high energy content with chemical and mechanical stability, two properties that are often contradictory. In this study, the syntheses and comprehensive characterizations of 4,5-bis(tetrazole-5-yl)-1,2,3-triazole and the novel 4,5-bis(1-hydroxytetrazole-5-yl)-1,2,3-triazole, as well as their energetic properties, are presented, combining the advantages of the more energetic tetrazole and the more stable 1,2,3-triazole rings. Nitrogen-rich salts of both compounds were synthesized to investigate their detonation performances and combustion behavior calculated by computer codes for potential application in erosion-reduced gun propellant mixtures due to their high nitrogen content. The structures of several of the compounds were studied by single-crystal X-ray diffraction and, especially in the case of 4,5-bis(tetrazol-5-yl)-1,2,3-triazole, revealed the site of deprotonation. Calling the shots: Combining the advantages of 1,2,3-triazole and tetrazole rings, 4,5-bis(tetrazol-5-yl)-1,2,3-triazole and its novel 1-hydroxytetrazole derivative were synthesized, as were their nitrogen-rich salts. Their energetic properties and potential application as gun propellants in erosion-reduced formulations were investigated. Furthermore, selected metal salts were tested for their use as primary explosives.

Beyond fluorine: Sustainable ternary polymer electrolytes for lithium batteries

In the state-of-the-art lithium-ion battery, sustainability and safety have often been 'sacrificed' in favor of 'performance' and 'cost'. Regarding the electrolyte, volatile and flammable solvents and highly toxic fluorinated lithium salts need replacements. Thus, the first fluorine-free ternary polyethylene oxide-based polymer electrolyte plasticized with ionic liquid (IL) is hereby presented using the non-fluorinated 4,5-dicyano-1,2,3-triazolate (DCTA) as the anion for both conducting lithium salt and the IL plasticizer, respectively. Due to its low molecular weight, membranes with a high molar percentage of IL can be achieved, up to a PEO?:?LiDCTA?:?Pyr14DCTA ratio of 20?:?2?:?4, without crosslinking the polymer part. DCTA membranes feature glass transition temperatures (Tgs) and ionic conductivities in the same range as their bis(trifluoromethanesulfonyl)imide (TFSI) analogs and much higher transference numbers. The 20?:?2?:?4 membrane has a Tg of -55.4 °C and an ionic conductivity of 5.2 × 10 4 S cm-1 at 40 °C. LFP||Li metal cells devoid of any critical raw materials and including this non-fluorinated TSPE were successfully cycled 300 times. This journal is

Halogen free 1,2,3- and 1,2,4-triazolide based ionic liquids: Synthesis and properties

Triazoles have been successfully used as building blocks to create "fully organic" ILs featuring on both sides organic ions, i.e., 1,2,3- or 1,2,4-triazolide anions and 1,2,4-triazolium or imidazolium cations. Glass transition temperatures, densities and viscosities of these ILs were determined. Their electrochemical and thermal stability, and also conductivity, are higher than those for known ILs.