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

pka

6.82±0.20(Predicted)

form 

Solid

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 Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

3276

Hazard Note 

Harmful

HS Code 

2933998090

3-Cyano-1,2,4-triazole Usage And Synthesis

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

3-Cyano-1,2,4-triazole(3641-10-9)Related Product Information

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