60016-63-9

Upstream product

• 3641-14-3 3-amino-1,2,4-triazole-5-carboxylic acid methyl ester 
• 63666-11-5 5-amino-1H-1,2,4-triazole-3-carboxylate ethyl ester 

Downstream Products

• 1016798-54-1 5-amino-1H-1,2,4-triazole-3-carbonitrile 
• 1016798-54-1 5-amino-1H-1,2,4-triazole-3-carbonitrile 

Relevant academic research and scientific papers

3-(5-Amino-1,2,4-triazole)-1,2,4-oxadiazole: A new biheterocyclic scaffold for the synthesis of energetic materials

Nitrogen-rich heterocycles are increasingly used in energetic chemistry with the aim to achieve superior performance of the new energetic materials. Combining such building blocks into biheterocycles increases energy output while at the same time retains low sensitivity. Herein, we report the synthesis and characterization of a compound containing a 5-amino-1,2,4-triazole moiety connected with a 1,2,4-oxadiazole ring. The trichloromethyl group attached to the oxadiazole ring offers an attractive point for further transformations into potentially energetic compounds.

Synthesis and characterization of 5-(1,2,4-Triazol-3-yl)tetrazoles with various energetic functionalities

In this contribution the synthesis and full structural as well as spectroscopic characterization of three 5-(1,2,4-triazol-3-yl)tetrazoles along with selected energetic moieties like nitro, nitrimino, and azido groups are presented. The main goal is a comparative study on the influence of those variable energetic moieties on structural and energetic properties. A complete characterization including IR and Raman as well as multinuclear NMR spectroscopy of all compounds is presented. Additionally, X-ray crystallographic measurements were performed and reveal insights into structural characteristics as well as inter- and intramolecular interactions. The standard enthalpies of formation were calculated for all compounds at the CBS-4M level of theory and reveal high positive heats of formation for all compounds. The calculated detonation parameters (using the EXPLO5.05 program) are in the range of 8000 m s-1 (8097 m s-1 (5), 8020 m s-1 (6), 7874 m s-1 (7)). As expected, the measured impact and friction sensitivities as well as decomposition temperatures strongly depend on the energetic moiety at the triazole ring. The C-C connection of a triazole ring with its opportunity to introduce a large variety of energetic moieties and a tetrazole ring, implying a large energy content, leads to the selective synthesis of primary and secondary explosives.

Salts of 5-(5-azido-1H-1,2,4-triazol-3-yl)tetrazol-1-ol: From highly sensitive primary explosives to insensitive nitrogen-rich salts

Several metal and nitrogen-rich salts of the recently presented 5-(5-azido-1H-1,2,4-triazol-3-yl)tetrazol-1-ol (AzTTO), including silver (1), copper(I) (2), potassium (3 and 5), cesium (4), copper(II) (6), ammonium (7 and 11), hydrazinium (8), guanidinium (9 and 12), and aminoguanidinium (10), were prepared and thoroughly characterized by IR and multinuclear (1H, 13C, 14N) NMR spectroscopy, mass spectrometry, and differential scanning calorimetry (DSC). Additionally, the structures of 3·H2O, 4, 5·3H2O, and 7 were determined by single-crystal X-ray diffraction. The compounds show interesting structural motifs, which were analyzed and are discussed. The sensitivities towards impact, friction, and electrostatic discharge were determined according to BAM (the German Federal Institute for Materials Research and Testing) standards, thereby revealing most of the metal salts to be highly sensitive and the nitrogen-rich salts to be mostly insensitive. Furthermore, the metal salts were tested for their ability to be primary explosives. The reaction of the recently presented 5-(5-azido-1H-1,2,4-triazol-3-yl)tetrazol-1-ol (AzTTO) with various metal and nitrogen-rich bases leads to several new ionic energetic compounds. Most of the metal salts are highly sensitive primary explosives with quite high thermal stabilities for this type of highly energetic anion. Copyright

ANTIFUNGAL AGENTS

Novel derivatives of enfumafungin are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antifungal agents and/or inhibitors of (l,3)-β-D-glucan synthase. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs,,as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating and/or preventing fungal infections and associated diseases and conditions.