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| | 3-Cyano-1,2,4-triazole Basic information |
| Product Name: | 3-Cyano-1,2,4-triazole | | Synonyms: | 3-CYANO-1,2,4-TRIAZOLE;1H-[1,2,4]-TRIAZOLE-3-CARBONITRILE;2H-1,2,4-triazole-3-carbonitrile;s-Triazole-3-carbonitrile;1,2-diaza-4-azanidacyclopenta-2,5-diene-3-carbonitrile;3-Cyano-1;1H-1,2,4-triazole-5-carbonitrile | | CAS: | 3641-10-9 | | MF: | C3H2N4 | | MW: | 94.07 | | EINECS: | | | Product Categories: | Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous | | Mol File: | 3641-10-9.mol |  |
| | 3-Cyano-1,2,4-triazole Chemical Properties |
| Melting point | 185-187°C | | Boiling point | 300.0±25.0 °C(Predicted) | | density | 1.44±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | DMSO, Methanol | | form | Solid | | pka | 6.82±0.20(Predicted) | | color | Off-White to Beige | | InChI | InChI=1S/C3H2N4/c4-1-3-5-2-6-7-3/h2H,(H,5,6,7) | | InChIKey | GUQHFZFTGHNVDG-UHFFFAOYSA-N | | SMILES | N1C(C#N)=NC=N1 | | CAS DataBase Reference | 3641-10-9(CAS DataBase Reference) |
| | 3-Cyano-1,2,4-triazole Usage And Synthesis |
| Uses | A cyano substituted triazole with inhibitory effects on cathepsin K, 3-cyano-1,2,4-triazole can be used in a study of the electrophilicity and reactivity of diverse nitrile-containing compounds and its correlation to the mechanism-of-action. | | Uses | A cyano substituted triazole with inhibitory effects on cathepsin K used in a study of the electrophilicity and reactivity of diverse nitrile-containing compounds and its correlation to the mechanism-of-action. | | Synthesis | 3-Cyano-1,2,4-triazole (3-CNT) was prepared based on the method described in U.S. Patent No. 4,522,587. The procedure was as follows: in a 250 ml three-necked flask equipped with a mechanical stirrer, a temperature probe, a cooling bath and a nitrogen protection device, 15.0 g (0.178 mol) of cyanoimidic acid hydrazide and 80.2 g (0.541 mol) of triethyl orthoformate were added. After cooling the reaction mixture to 0-5 °C, 4 g of dioxane solution pre-saturated with HCl gas was added at once. The reaction temperature was maintained at 0-5°C with stirring for 5 h. The reaction was then slowly warmed to room temperature and stirring continued until the residue of cyanoimidic acid hydrazide was less than 0.5 area % (reaction complete) as detected by HPLC. Upon completion of the reaction, the excess triethyl orthoformate was removed by distillation under reduced pressure to give the crude 3-CNT (12.3 g, HPLC purity 76 area%). The crude was suspended in a solvent mixture of 248 g of toluene and 202 g of ethyl acetate, heated to 75-80 °C and filtered to remove insoluble matter. The filtrate was concentrated under reduced pressure to obtain a slurry, after filtration, the filter cake was washed with 10 ml of toluene and dried to finally obtain 10.1 g of 3-CNT as a pale yellow solid (yield 60.2%, HPLC purity 98.7 area%). | | References | [1] Patent: US2009/292122, 2009, A1. Location in patent: Page/Page column 11 |
| | 3-Cyano-1,2,4-triazole Preparation Products And Raw materials |
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