Category: 53817-16-6

Cao, Wenli published the artcile4,5-Dicyano-1,2,3-Triazole-A Promising Precursor for a New Family of Energetic Compounds and Its Nitrogen-Rich Derivatives: Synthesis and Crystal Structures, Safety of 1H-1,2,3-Triazole-4,5-dicarbonitrile, the publication is Molecules (2021), 26(21), 6735, database is CAplus and MEDLINE.

The nitrogen-rich compounds and intermediates with structure of monocyclic, bicyclic, and fused rings based on 1,2,3-triazole were synthesized and prepared by using a promising precursor named 4,5-dicyano-1,2,3-triazole, which was obtained by the cyclization reaction of diaminomaleonitrile. Their structure and configurational integrity were assessed by Fourier transform-IR spectroscopy (FT-IR), mass spectrometry (MS), and elemental anal. (EA). Addnl., fourteen compounds were further confirmed by X-ray single crystal diffraction. Meanwhile, the phys. properties of four selected compounds including thermal stability, detonation parameters, and sensitivity were also estimated All these compounds could be considered to construct more abundant 1,2,3-triazole-based neutral energetic mols., salts, and complex compounds, which need to continue study in the future in the field of energetic materials.

Molecules published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Safety of 1H-1,2,3-Triazole-4,5-dicarbonitrile.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Hebert, T. J. published the artcileThe influence of solvent upon the optical rotation of diethyl tartrate, Synthetic Route of 53817-16-6, the publication is Proceedings of the Iowa Academy of Science (1927), 218-9, database is CAplus.

Determination, of the [α] of di-Et tartrate in various mixed solvents have been made at 25° and 30°, with 2 different concentrations of the ester. The solvents used were EtOH, MeOH, C₆H₆ and PhMe and the binary mixtures of each solvent with each of the remaining solvents. The mixed solvents were made on a mol. fraction basis. The [α] was found to be dependent on the composition of the mixed solvent, upon the concentration of the ester and upon the temperature It was also found to be influenced by the nature and proportions of the 2 solvents forming the binary mixture

Proceedings of the Iowa Academy of Science published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Synthetic Route of 53817-16-6.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Hu, Lu published the artcileEnergetic compounds based on a new fused triazolo[4,5-d]pyridazine ring: Nitroimino lights up energetic performance, Related Products of triazoles, the publication is Chemical Engineering Journal (Amsterdam, Netherlands) (2021), 420(Part_1), 129839, database is CAplus.

A series of highly energetic materials with good detonation performance, high d. and low impact sensitivity based on a new triazolo[4,5-d]pyridazine fused ring was synthesized and characterized. 4-Nitroamino-7-nitroimino-triazolo[4,5-d]pyridazine was characterized by single crystal X-ray structure anal., which shows that the proton of one nitroamino group was transferred to the pyridazine ring forming a nitroimino moiety. The electrostatic potential (ESP) of 4-Nitroamino-7-nitroimino-triazolo[4,5-d]pyridazine shows the nitroimino group has the lowest neg. value, while the nitroamino area has a high pos. value. The anal. of NCI plots indicates strong intramol. hydrogen bonds (HB) and π-π interactions which arise from the newly formed nitroimino group. This supports that the rearrangement of the nitroamino group to form the nitroimino moiety lowers the impact sensitivity. Compound 4-Nitroamino-7-nitroimino-triazolo[4,5-d]pyridazine·H₂O exhibits face-to-face packing, which gives rise to a relatively high d. of 1.87 g cm^-3 and a low impact sensitivity of 18 J. Its hydrazinium and hydroxylammonium salts have high detonation velocities of 9351 m s^-1 and 9307 m s^-1, resp. Their impact and friction sensitivities (7 J, 120 N and 8 J, 160 N) are similar to HMX. This proclivity for rearrangement by a nitroamino group provides new insight into the design of next generation high energy d. materials.

Chemical Engineering Journal (Amsterdam, Netherlands) published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Related Products of triazoles.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Holzmann, G. published the artcileNegative ion mass spectra of cyano substituted heterocycles, Safety of 1H-1,2,3-Triazole-4,5-dicarbonitrile, the publication is Organic Mass Spectrometry (1978), 13(11), 636-41, database is CAplus.

The neg. ion mass spectra are reported of 21 dicyano heteroaromatic compounds The spectra are useful for the anal. of isomeric compounds All the compounds fragment to give [(CN)₂]•^–, [C₄N₃]^–, or [C₄N₄]•^– ions. The ion structures were identified using metastable transitions and collisional activation spectra. The fragmentations of tetracyano compounds are explained by rearrangement processes of mol. anions.

Organic Mass Spectrometry published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Safety of 1H-1,2,3-Triazole-4,5-dicarbonitrile.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Hinkel, L. E. published the artcileHydrogen cyanide. X. The tetrapolymer, COA of Formula: C4HN5, the publication is Journal of the Chemical Society (1937), 1432-7, database is CAplus.

cf. C. A. 31, 597.2. The previous evidence for the structure of the polymerized form of HCN is reviewed and further evidence is adduced for its quadrimol. nature. The view that the polymer is diaminomaleic dinitrile is shown to be incorrect and experiments indicate it to be aminoiminosucconitrile (I). The polymerization product of HCN, m. 181° (decomposition), condenses with glyoxal in hot H₂O to give 6-hydroxy-2,3-dicyanodihydropyrazine, red, amorphous, decomposes 240° without melting; it is very slowly decomposed by boiling H₂O, but H₂O containing a little (CO₂H)₂ gives dicyanopyrazine (II), m. 132°. Hydrolysis of II by Na₂O₂ in H₂O and purification through the Ag salt give pyrazinedicarboxylic acid, m. 193°. The polymer of HCN in Et₂O, saturated with dry HCl, gives the HCl salt of I, decomposes 135°. Refluxing the polymer with aldehydes in EtOH for 30 min. gives the following derivatives of I: benzylidene (III), yellow, m. 191° (decomposition); salicylidene, yellow with green tinge, m. 234° (decomposition); m-bromosalicylidene, yellow, m. above 250°; anisylidene, yellow, m. 227° (decomposition); isobutylidene, m. 91° (decomposition); in no case could a 2nd mol. of aldehyde be condensed. The Ac derivative of I m. 164° (decomposition); the di-Ac derivative m. 224° (decomposition); the Ac derivative of III m. 227° (decomposition). Ac₂ and I give 2,3-dicyano-5,6-dimethylpyrazine (IV), m. 171°; benzil forms 2,3-dicyano-5,6-diphenylpyrazine, m. 246°. Hydrolysis of IV gives 2,3-dimethylpyrazine-5,6-dicarboxylic acid, m. 200°. The action of HNO₂ on I yields 4,5-dicyano-1,2,3-triazole (V), hydrolysis of which gives 1,2,3-triazole-4,5-dicarboxylic acid. The action of HNO₂ on the Ac derivative of I forms 4 (or 5)-cyano-1,2,3-triazole-5 (or 4)-carboxamide, m. 219° (decomposition), and V. Oxidation of III gives 4,5-dicyano-2-phenyliminazole, cream, m. 261° (decomposition); hydrolysis gives 2-phenyliminazole-4,5-dicarboxylic acid, m. 243-4°.

Journal of the Chemical Society published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, COA of Formula: C4HN5.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Bilton, J. A. published the artcilePhthalocyanines. X. Experiments in the pyrrole, isoöxazole, pyridazine, furan and triazole series, Category: triazoles, the publication is Journal of the Chemical Society (1937), 922-9, database is CAplus.

The general result of this series was that no phthaloeyanine-like pigment was obtained in any of the 5 series investigated. In some cases this appears to be a genuine neg. and in agreement with theory; in others the result is inconclusive, as suitably close intermediates could not be prepared Di-Et 2,5.-dimethylpyrrole-3,4-dicarboxylic acid does not react with NH₃ to form the diamide; it also could not be prepared through the acid chloride. The Na compound of NCCH₂Ac did not react with I or α-bromocyanoacetone (from NCCH₂Ac and Br, b₁₂ 43° to give diacetylsuccinonitrile, neither could the pyrrole be obtained by direct condensation of these compounds with NH₃. Me 1,2-diacetylsuccinate, b₂₀, 120°, m. 113.5°; aqueous NH₄OH gave only a brown oil. Et 3-formyl-2,5-dimethylpyrrole-4-carboxylate and its oxime were prepared from Et 2,5-dimethylpyrrole-3-carboxylate; dehydration of the oxime yields Et 3-cyano-2,5-dimethylpyrrole-4-carboxylate, m. 152°, which does not yield an amide on heating under pressure with NH₃-MeOH or aqueous NH₄OH. Hydrolysis gives the free acid, m. 288°(decomposition), which, on heating at 200° and 13 mm., gives 73% of 3-cyano-2,5-dimethylpyrrole, m. 89°. Through the imine-HCl this was converted into the 4-formyl derivative, yellow, m. 207° (81% yield) (oxime, m. 223°); Ac₂O and AcONa convert this into 3,4-dicyano-2,5-dimethylpyrrole, m. 239° (89% yield); this yielded no phthalocyanine-like pigment when treated with metallic reagents under the usual conditions. 4-Carbethoxy-2,3-dimethylpyrrole-5-aldoxime on refluxing with Ac₂O and AcONa gives 81% of Et 5-cyano-2,3-dimethylpyrrole-4-carboxylate, m. 180°; the free acid, m. 242°, decomposes 250°, results in 94% yield and could not be decarboxylated to the corresponding mononitrile. 2,3-Dimethylpyrrole was converted into the 5-formyl derivative and the 5-aldoxime, dehydrated to the 5-CN derivative, m. 121.5°, in 66% yield; this does not react with HCN and HCl, nor does the 5-aldoxime or 5-aldehyde. 5-Methylisoöxazole-3,4-dicarboxamide, m. 216°, results in 67% yield from the Et ester and NH₄OH; P₂O₅ gives 70% of 3,4-dicyano-5-methylisoöxazole, b₁₂ 115°, b₇₆₀ 245° (some decomposition), m. 32°; about 3 hrs. heating at 115-20° and 5 mm. were necessary to form a pure product; HCl in absolute EtOH gives a mixture of the above Et ester and 3(or 4)-cyano-5-methylisoöxazole-3(or 4)-carboxamide, m. 225°; this also resulted with 10% KOH. The dinitrile did not form a phthalocyanine-like pigment. 3,6-Dimethylpyridazine-4,5-dicarboxamide, m. 240°, results in theoretical yield from the ester and NH₄OH; sublimation at 240° and 10 mm. gives 44% of the imide, m. 240° (decomposition); the dinitrile could not be prepared and the imide did not yield a Cu pigment of the phthalocyanine type. Refluxing 2,5-dimethylfuran-3,4-dicarboxamide with Ac₂O for 6 hrs: gives 4-cyano-2,5-dimethylfuran-3-carboxylic acid, m. 174°. Me 5-cyano-3-methylfuran-4-carboxylate, m. 49° (in 26% yield from the Ag salt and MeI), is hydrolyzed by concentrated NH₄OH and is unchanged by EtOH-NH₃ at 50° for 2 days. Dicyanotriazole does not yield pigments with metallic reagents; it is soluble in aqueous NaHCO₃ with effervescence and a dilute aqueous solution dissolves Zn with evolution of H; the Ag salt, precipitated with AgNO₃, is not dissolved by cautious addition of dilute HNO₃; warming the Ag salt with excess HNO₃ gives the free dinitrile; MeOH does not give a Me ether.

Journal of the Chemical Society published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Category: triazoles.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Cassani, Stefano published the artcileDaphnia and fish toxicity of (benzo)triazoles: Validated QSAR models, and interspecies quantitative activity-activity modeling, Computed Properties of 53817-16-6, the publication is Journal of Hazardous Materials (2013), 50-60, database is CAplus and MEDLINE.

Due to their chem. properties synthetic triazoles and benzo-triazoles ((B)TAZs) are mainly distributed to the water compartments in the environment, and because of their wide use the potential effects on aquatic organisms are cause of concern. Non testing approaches like those based on quant. structure-activity relationships (QSARs) are valuable tools to maximize the information contained in existing exptl. data and predict missing information while minimizing animal testing. Externally validated QSAR models for the prediction of acute (B)TAZs toxicity in Daphnia magna and Oncorhynchus mykiss have been developed according to the principles for the validation of QSARs and their acceptability for regulatory purposes, proposed by the Organization for Economic Co-operation and Development (OECD). These models are based on theor. mol. descriptors, and are statistically robust, externally predictive and characterized by a verifiable structural applicability domain. They were applied to predict acute toxicity for >300 (B)TAZs without exptl. data, many of which are in the pre-registration list of the REACH regulation. A model based on quant. activity-activity relationships (QAAR) has been developed, which allows for interspecies extrapolation from daphnids to fish. The importance of QSAR/QAAR, especially when dealing with specific chem. classes like (B)TAZs, for screening and prioritization of pollutants under REACH, has been highlighted.

Journal of Hazardous Materials published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Computed Properties of 53817-16-6.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Qin, Jian published the artcileThe nitrogen-rich energetic compound 4-carboxamide-5-(1H-tetrazol-5-yl)-1H-1,2,3-triazole and its 1D sodium complex: synthesis and properties, Safety of 1H-1,2,3-Triazole-4,5-dicarbonitrile, the publication is RSC Advances (2016), 6(103), 101430-101436, database is CAplus.

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-IR spectroscopy (FT-IR), mass spectrometry (MS) and elemental anal. (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 d. 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).

RSC Advances published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Safety of 1H-1,2,3-Triazole-4,5-dicarbonitrile.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Ried, Walter published the artcileSynthesis of new, heterocyclic phanes from 1,2,3-triazolo-4,5-dicarbonitrile, Product Details of C4HN5, the publication is Chemiker-Zeitung (1989), 113(12), 384-5, database is CAplus.

Methylation of the title compound gave the 2-Me derivative I. Double cycloaddition of I with NH₄N₃ gave the corresponding 4,5-bis(5-tetrazolyl)-1,2,3-triazole, which underwent reaction with Br(CH₂)_nBr (n = 6-8, 10) to give sym. heterophanes II.

Chemiker-Zeitung published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Product Details of C4HN5.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics