1H-Benzimidazole-4-carboxylic acid Chemical Properties

Melting point:

>300 °C

Boiling point:

542.5±23.0 °C(Predicted)

Density 

1.506±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

0.17±0.10(Predicted)

Appearance

Off-white to light brown Solid

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36-51

Safety Statements 

53-26-61

RIDADR 

UN 3077 9 / PGIII

HazardClass 

IRRITANT

HS Code 

29339980

1H-Benzimidazole-4-carboxylic acid Usage And Synthesis

Synthesis

To a 4M hydrochloric acid (20 mL) solution of formic acid (0.75 mL, 20.0 mmol) was added 2,3-diaminobenzoic acid (1.00 g, 6.6 mmol). The reaction mixture was heated at reflux temperature for 2 h and subsequently cooled to room temperature. The resulting pink precipitate was separated by filtration and dissolved in hot methanol. Decolorization was carried out by adding activated carbon and stirring for 10 min. The suspension was filtered and the solvent was evaporated under reduced pressure to afford benzimidazole-7-carboxylic acid (0.542 g, 51% yield) as white crystals with a melting point of 266-268 °C. The structure of the product was analyzed by 1H NMR (300 MHz, DMSO-d6) δ 9.64 (s, 1H), 8.11 (dd, J = 8.2, 0.9 Hz, 1H), 8.07 (dd, J = 7.6, 0.9 Hz, 1H), 7.65 (dd, J = 8.2, 7.6 Hz, 1H) and 13C NMR (75 MHz, DMSO-d6 ) δ 265.2, 142.0, 132.3, 129.3, 127.6, 125.6, 119.7, 117.6 confirmed.

References

[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[3] Chemische Berichte, 1901, vol. 34, p. 905
[4] Patent: WO2018/42362, 2018, A1. Location in patent: Page/Page column 50

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