Reaction of 1-methyl-3,5-dinitro-1,2,4-triazole with alcohols or phenols in the presence of bases (tertiary amines) leads to replacement of the nitro group in the 5-position by an alkoxy or phenoxy group.

The critical evaluation of a large body of the information on five-membered nitroazoles and nitrobenzazoles study by physical chemical methods – nuclear magnetic resonance (NMR), nuclear quadrupole resonance (NQR), electron spin resonance (ESR), ion-cyclotron resonance, UV and IR- spectroscopy, X-ray analysis, mass spectrometry, polarography, dipole moments, chromatography, luminescence, photolysis, etc. is presented. The extensive investigations of structure, tautomerism, and properties of nitroazoles by multinuclear 1H, 13C, 15N, 19F, 31P, 29Si and two-dimensional NMR spectroscopy are reviewed. A great emphasis is given to tautomerism studies of nitroazoles by multinuclear dynamic NMR because prototropic transformations of almost all azoles in solutions proceed so quickly. The mechanisms of electrochemical reactions and vicarious nucleophilic C-amination of nitroazoles are discussed. Quantum-chemical investigations of nitroazoles are covered in detail.

Heterocyclic nitro compounds: V. 1-Methyl-3-nitro-5-alkoxy- and -phenoxy-1,2,4-triazoles

Structure and Physical–Chemical Properties of Nitroazoles

A HPLC method was established to analyze main ingredient – 1-methyl-3,5-dinitro-1H-1,2,4-triazole and the main impurity –1-methyl-3-nitro-1H-1,2,4-triazol-5-amine. The method was carried out on a SinoChrom ODS-BP column (4.6 × 200 mm, 5 μm) using methanol–water (90/10, v/v) as the mobile phase at a flow rate of 1.0 ml·min–1. 1-Methyl-3,5-dinitro-1H-1,2,4-triazole was determined by UV-visible detector at 240 nm. The column temperature was 25°C and the injection volume was 10 μl. Results show that under the optimized chromatographic conditions, the calibration curves of 1-methyl-3,5-dinitro-1H-1,2,4-triazole and 1-methyl-3-nitro-1H-1,2,4-triazol-5-amine have good linearity, and the linear correlation coefficient r is greater than 0.999. The detection limits for 1-methyl-3,5-dinitro-1H-1,2,4-triazole and 1-methyl-3-nitro-1H-1,2,4-triazol-5-amine were 0.6 and 0.31 mg·ml–1, respectively, and the quantification limits were 1.02 and 0.53 mg·ml–1, respectively. The recoveries are 98.17–100.83% with the relative standard deviations between 0.44 and 1.01%. The method has wide linear range, high sensitivity, and good reproducibility, and the results are accurate and reliable.

Purity analysis method of 1-methyl-3,5-dinitro-1 H -1,2,4-triazole

http://link.springer.com/content/pdf/10.1007/BF00500695.pdf

Heterocyclic nitro compounds: V. 1-Methyl-3-nitro-5-alkoxy- and -phenoxy-1,2,4-triazoles

Citations

Structure and Physical–Chemical Properties of Nitroazoles

Purity analysis method of 1-methyl-3,5-dinitro-1 H -1,2,4-triazole

References

408. Compounds related to thiosemicarbazide. Part III. 1-Benzoyl-S-methylisothiosemicarbazides