1H-Benzimidazole-5-carboxylic acid Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

288.82°C (rough estimate)

Density 

1.3264 (rough estimate)

refractive index 

1.5770 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Powder

pka

3.10±0.30(Predicted)

color 

Green-gray to gray-brown

BRN 

5686

InChI

InChI=1S/C8H6N2O2/c11-8(12)5-1-2-6-7(3-5)10-4-9-6/h1-4H,(H,9,10)(H,11,12)

InChIKey

COYPLDIXZODDDL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

15788-16-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

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

1H-Benzimidazole-5-carboxylic acid Usage And Synthesis

Chemical Properties

GREEN-GREY TO GREY-BROWN POWDER

Uses

A benzimidazole derivative that exhibits corrosion inhibiting properties against strong acids.

Uses

5-Benzimidazolecarboxylic acid has been used in the preparation of:

• 1H-benzoimidazole-5-carboxylic acid benzotriazol-1-yl ester
• piperidin-1-yl(1-m-tolyl-1H-benzo[d]imidazol-5-yl)methanone

General Description

Drug-specific monoclonal antibodies were produced against the very small drug hapten, 5-benzimidazolecarboxylic acid.

Synthesis

To a solution of 5-bromo-1H-benzimidazole (0.87 g, 4.4 mmol, 1.0 eq.) in anhydrous THF (20 mL) was slowly added 2 M isopropylmagnesium chloride (i-PrMgCl) in a solution of THF (2.2 mL, 4.4 mmol, 1.0 eq.) at 0 °C, keeping the reaction temperature not more than 20 °C. After addition, the clarified solution was continued to be stirred at 0 °C for 5 min. Subsequently, 2.5 M hexane solution (3.5 mL, 8.8 mmol, 2.0 eq.) of n-butyllithium (n-BuLi) was added dropwise over 5 min, controlling the temperature below 20 °C. The reaction mixture was stirred at the same temperature for 30 min. Then, dry carbon dioxide (0.20 g, 4.4 mmol, 1.0 eq.) was added to the reaction system and the mixture was slowly warmed to 20 °C over 30 min. Upon completion of the reaction, the reaction was quenched with deionized water (6 mL). After stirring at 20 °C for 10 min, the organic and aqueous phases were separated. The aqueous phase was extracted once with ethyl acetate (10 mL). The organic phases were combined, filtered through a 0.51 cm silica gel pad and eluted with ethyl acetate (10 mL). The filtrate was concentrated and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 3:1) to afford 1H-benzimidazole-5-carboxylic acid (0.5 g, 71% yield) as a brown solid. The product was structurally confirmed by 1H-NMR (600 MHz, DMSO-d6) and 13C-NMR (151 MHz, DMSO-d6).

References

[1] Molecules, 2017, vol. 22, # 11,

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