2-HYDRAZINO-1H-1,3-BENZIMIDAZOLE Chemical Properties

Melting point:

224-225

Boiling point:

318.2±25.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly, Heated), Methanol (Slightly)

form 

Solid

pka

6.07±0.20(Predicted)

color 

Dark Brown

InChI

InChI=1S/C7H8N4/c8-11-7-9-5-3-1-2-4-6(5)10-7/h1-4H,8H2,(H2,9,10,11)

InChIKey

PXUYWNZBZXDJEU-UHFFFAOYSA-N

SMILES

C1(NN)NC2=CC=CC=C2N=1

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933998090

2-HYDRAZINO-1H-1,3-BENZIMIDAZOLE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-hydrazino-1H-1,3-benzimidazole was as follows: firstly, 2-bromobenzimidazole was prepared from 2-mercaptobenzimidazole according to the method reported in literature [13]. Subsequently, 2-bromobenzimidazole (1.97 g, 10 mmol) was dissolved in 20 mL of 80% hydrazine hydrate solution and reacted at reflux to obtain 2-hydrazinylbenzimidazole (1.35 g, 91% yield). Finally, diacetyl monoxime (1.01 g, 10 mmol) was added to a 20 mL methanol solution containing 2-hydrazinylbenzimidazole (1.48 g, 10 mmol) catalyzed by glacial acetic acid (3 drops). The reaction mixture was refluxed for 4 h. After cooling and filtration, the resulting white crystals were washed with cold methanol to afford the target product 2-hydrazino-1H-1,3-benzimidazole (1.6 g, 55% yield, melting point 240 °C).

References

[1] Journal of Molecular Structure, 2017, vol. 1133, p. 546 - 556
[2] Polyhedron, 2017, vol. 127, p. 225 - 237

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