1-METHYL-2-FORMYLBENZIMIDAZOLE Chemical Properties

Melting point:

114-116 °C

Boiling point:

286.07°C (rough estimate)

Density 

1.1846 (rough estimate)

refractive index 

1.5570 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Crystalline Powder

pka

3?+-.0.10(Predicted)

color 

Off-white to light beige

Sensitive 

Air Sensitive

CAS DataBase Reference

3012-80-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-METHYL-2-FORMYLBENZIMIDAZOLE Usage And Synthesis

Chemical Properties

OFF-WHITE TO LIGHT BEIGE CRYSTALLINE POWDER

Uses

1-Methyl-1H-benzimidazole-2-carboxaldehyde is a reagent used for the synthesis of dual protein kinase B alpha (AKT) and nuclear factor kappa-light-chain-enchancer of activated B cells (NF-κB) against melanoma.

Synthesis

General procedure for the synthesis of 1-methyl-2-formylbenzimidazole from N-methylbenzimidazole and 2,2-diethoxyacetic acid: N-methylbenzimidazole (0.10 mmol, 1.0 eq.), ammonium persulfate (0.30 mmol, 3.0 eq.), and Cs2CO3 (0.20 mmol, 2.0 eq.) were placed in a dry glass tube. Subsequently, anhydrous DMSO (1 mL) and 2,2-diethoxyacetic acid (0.7 mmol) were added to the tube via syringe under nitrogen protection. The reaction mixture was stirred for 24 h at room temperature using 15 W blue LED strip irradiation. After completion of the reaction, the reaction was quenched by the addition of 1.2 mL of 3.0 M HCl and stirring was continued for 20 hours. Afterwards, the pH was adjusted with saturated Na2CO3 solution and extracted with CH2Cl2. The organic layers were combined, washed with brine and dried over anhydrous Na2SO4. Finally, the target product 1-methyl-2-formylbenzimidazole was purified by rapid chromatography on silica gel, using petroleum ether and ethyl acetate as eluents, and the corresponding yield was calculated.

References

[1] Synlett, 2018, vol. 29, # 14, p. 1881 - 1886

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