1H-Benzimidazole-2-carboxylicacid,1-methyl-,methylester(9CI)

1H-Benzimidazole-2-carboxylicacid,1-methyl-,methylester(9CI) Property

Melting point:

88 °C

Boiling point:

326.4±25.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.51±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

1H-Benzimidazole-2-carboxylicacid,1-methyl-,methylester(9CI) Chemical Properties,Usage,Production

Synthesis

To a solution of 1H-benzimidazole-2-carboxylic acid methyl ester (177 mg, 1.0 mmol) in anhydrous N,N-dimethylformamide (DMF, 5 mL) was added sodium hydride (60% dispersed in mineral oil, 62 mg, 1.5 mmol) at 0 °C under nitrogen protection. The reaction mixture was stirred at 0 °C for 0.5 h. After that, iodomethane (284 mg, 2.0 mmol) was slowly added. Subsequently, the reaction mixture was continued to be stirred at room temperature for 4 hours. After completion of the reaction, the mixture was diluted with saturated saline at 0 °C and extracted with ethyl acetate (3 x 20 mL). The combined organic phases were washed sequentially with water (2 x 15 mL) and saturated saline (20 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by fast column chromatography to afford methyl 1-methyl-1H-benzimidazole-2-carboxylate (180 mg, 90% yield) as a light yellow solid.ESI-MS (M + 1): 191 (calculated value: C10H10N2O2).

References

[1] Patent: WO2011/143365, 2011, A1. Location in patent: Page/Page column 170-171