2-(Cyanomethyl)benzimidazole Chemical Properties

Melting point:

200-205 °C (dec.)(lit.)

Boiling point:

271.83°C (rough estimate)

Density 

1.2279 (rough estimate)

refractive index 

1.5330 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

11.01±0.10(Predicted)

color 

White to Brown

Water Solubility 

Insoluble in water.

BRN 

128461

InChIKey

BWOVACANEIVHST-UHFFFAOYSA-N

CAS DataBase Reference

4414-88-4(CAS DataBase Reference)

EPA Substance Registry System

1H-Benzimidazole-2-acetonitrile (4414-88-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39-24/25

RIDADR 

3276

WGK Germany 

3

RTECS 

DD5650000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29332900

Toxicity

LD50 ivn-mus: 56 mg/kg CSLNX* NX#04148

MSDS

• Language:English Provider:2-Benzimidazolylacetonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-(Cyanomethyl)benzimidazole Usage And Synthesis

Chemical Properties

LIGHT BEIGE FINE CRYSTALLINE POWDER

Uses

2-Benzimidazoleacetonitrile, is used as a pharmaceutical intermediate. It is also used as an intermediate in organic synthesis.

Safety Profile

Poison by intravenous route. Seealso NITRILES. When heated to decomposition it emitstoxic fumes of NOx.

Synthesis

To the dry solid of o-phenylenediamine (1.08 g, 10 mmol) was added ethyl cyanoacetate (1.13 g, 10 mmol). The reaction mixture was placed in an oil bath and heated at 120 °C for 30 min, followed by cooling to room temperature. Upon completion of the reaction, the product was collected by filtration and ground with diethyl ether for purification. Finally, recrystallization was carried out from ethanol to give 2-cyanomethylbenzimidazole.

References

[1] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 3, p. 309 - 318
[2] ChemMedChem, 2016, vol. 11, # 5, p. 539 - 548
[3] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 853 - 869
[4] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 270 - 282
[5] Chinese Chemical Letters, 2010, vol. 21, # 5, p. 519 - 523

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