5-METHOXYBENZIMIDAZOLE Chemical Properties

Melting point:

121-126 °C (lit.)

Boiling point:

190-195 °C(Press: 0.03 Torr)

Density 

1.244±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

13.12±0.10(Predicted)

color 

Light brown to brown

InChI

InChI=1S/C8H8N2O/c1-11-6-2-3-7-8(4-6)10-5-9-7/h2-5H,1H3,(H,9,10)

InChIKey

ILMHAGCURJPNRZ-UHFFFAOYSA-N

SMILES

C1NC2=CC(OC)=CC=C2N=1

CAS DataBase Reference

4887-80-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29332990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-METHOXYBENZIMIDAZOLE Usage And Synthesis

Chemical Properties

White to brown powder

Uses

6-Methoxy-1H-benzimidazole has been studied for its anti-proliferative activity, and a preliminary in vivo toxicity study against a panel of non-small cell lung cancer cell lines.

Synthesis

To a 16 mL reaction flask equipped with a PTFE/silicone septum and a nitrogen bubbler was added N-benzylbenzimidazole (208.1 mg, 1.0 mmol), dried Pd/C catalyst (10 wt%, 20 mg) and THF (5 mL). Triethylsilane (320 μL, 2.0 mmol) was added dropwise to the mixture under nitrogen protection, followed by continuous stirring at room temperature for 14 hours. After completion of the reaction, the reaction mixture was filtered through a 0.45 μm PTFE syringe filter and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluent: 0 to 10% methanol/dichloromethane gradient) to afford 5-methoxybenzimidazole as a colorless solid (117.6 mg, 0.996 mmol, 99% yield). It is worth noting that the reaction typically suffers from an induction period of 5 to 30 min, which can be observed by the release of gas from the reaction mixture (i.e., the bubbling phenomenon). The use of a dry Pd/C catalyst is critical to the success of the reaction, and wet Pd/C may result in a significant decrease in yield or inability of the reaction to proceed.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690

5-METHOXYBENZIMIDAZOLE(4887-80-3)Related Product Information

• 5-METHOXYBENZIMIDAZOLE
• 5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole
• Esomeprazole
• 2-MERCAPTO-5-METHOXYBENZIMIDAZOLE
• 5-HYDROXY OMEPRAZOLE
• 5,6-Dimethoxybenzimidazole
• Oxibendazole
• 1,3-Dihydro-5-methoxy-2H-benzimidazole-2-one~2-Hydroxy-5-methoxybenzimidazole,2-HYDROXY-5-METHOXYBENZIMIDAZOLE
• 2-[(4-METHOXYETHOXY-3,5-DIMETHYL-2-PYRIDINYL)-METHYLTHIO]-5-METHOXYBENZIMIDAZOLE
• Triclabendazole
• 2-[(4-METHOXY-3,5-DIMETHYLPYRID-2-YL)-METHYLSULFO]-5-METHOXYBENZIMIDAZOLE
• 2-MERCAPTO-5-METHOXYBENZIMIDAZOLE-4,6,7-D3
• 5-Methoxybenzimidazole-2-carboxylic acid monohydrate
• 2-CHLORO-5-METHOXYBENZIMIDAZOLE
• 2-[(4-METHOXY-3,5-DIMETHYLPYRID-2-YL)-METHYLSULFO]-5-METHOXYBENZIMIDAZOLE
• 5-Methoxybenzimidazole-2-methanol
• 2-METHYL-5,6-DIMETHOXYBENZIMIDAZOLE
• 6,7-DIHYDRO-1H-[1,4]DIOXINO[2',3':4,5]BENZO[D]IMIDAZOLE-2-THIOL