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

2-HYDRAZINO-1H-1,3-BENZIMIDAZOLE Property

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

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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

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