Methyl Benzimidazole-5-carboxylate Chemical Properties

Melting point:

139 °C

Boiling point:

416.2±18.0 °C(Predicted)

Density 

1.324±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

11.67±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C9H8N2O2/c1-13-9(12)6-2-3-7-8(4-6)11-5-10-7/h2-5H,1H3,(H,10,11)

InChIKey

WJHHIVYNOVTVGY-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933998090

Methyl Benzimidazole-5-carboxylate Usage And Synthesis

Uses

Methyl Benzimidazole-5-carboxylate can be used as an intermediate used for the synthesis of a number of bioisosteric benzimidazoles as inhibitors of human cytosolic phospholipase A2α.

Synthesis

General procedure for the synthesis of methyl benzimidazole-5-carboxylate from methanol and 1H-benzimidazole-5-carboxylic acid: (a) Synthesis of methyl 1H-benzimidazole-5-carboxylate Thionyl chloride (0.135 mL, 1.85 mmol) was slowly added dropwise to a solution of 1H-benzimidazole-5-carboxylic acid (0.300 g, 1.85 mmol) in methanol (50.0 mL). The reaction mixture was refluxed for 12 hours. After completion of the reaction, the mixture was poured into saturated aqueous sodium bicarbonate solution and stirred thoroughly. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a purple solid product in 90% yield. The crude product can be used in subsequent reactions without further purification. [MS (ES+) m/e 177 [M + H]+].

References

[1] Patent: WO2005/82901, 2005, A1. Location in patent: Page/Page column 91
[2] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 125
[3] Patent: WO2007/103755, 2007, A2. Location in patent: Page/Page column 111
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2925 - 2930
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 24, p. 3161 - 3164

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