| Identification | More | [Name]
3-Cyano-1,2,4-triazole | [CAS]
3641-10-9 | [Synonyms]
1H-[1,2,4]-TRIAZOLE-3-CARBONITRILE
3-CYANO-1,2,4-TRIAZOLE | [Molecular Formula]
C3H2N4 | [MDL Number]
MFCD03428509 | [Molecular Weight]
94.07 | [MOL File]
3641-10-9.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3276 | [Hazard Note ]
Harmful | [HS Code ]
2933998090 |
| Hazard Information | Back Directory | [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. | [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.
| [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 |
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