1H-Benzimidazol-5-ol Chemical Properties

Melting point:

220-222℃

Boiling point:

469.1±18.0 °C(Predicted)

Density 

1.434±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

9.20±0.40(Predicted)

Appearance

Brown to black Solid

InChI

InChI=1S/C7H6N2O/c10-5-1-2-6-7(3-5)9-4-8-6/h1-4,10H,(H,8,9)

InChIKey

KRKSOBREFNTJJY-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

1H-Benzimidazol-5-ol Usage And Synthesis

Uses

1H-Benzo[D]Imidazol-5-ol is a pathway intermediate in the anaerobic biosynthesis of the lower ligand of vitamin B12 (cobalamin).

Definition

ChEBI: 5-hydroxybenzimidazole is a member of the class of benzimidazoles that is 1H-benzimidazole carrying a single hydroxy substituent at position 5. It has a role as a human metabolite, a rat metabolite and a bacterial metabolite. It is a member of benzimidazoles and a member of phenols. It derives from a hydride of a 1H-benzimidazole.

Synthesis

General procedure for the synthesis of 1H-benzimidazol-5-ol from 5-methoxybenzimidazole: 5-methoxybenzimidazole (500 mg, 3.374 mmol) was dissolved in 48% hydrobromic acid (10 mL) and the reaction was carried out at reflux for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by rotary evaporator under reduced pressure. The residue was azeotropically treated with toluene (50 mL) to give the final title compound 1H-benzimidazol-5-ol as a brown solid (701 mg, 96% yield).

References

[1] Patent: WO2007/76034, 2007, A2. Location in patent: Page/Page column 125
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 5192
[3] Synthetic Communications, 2010, vol. 40, # 12, p. 1765 - 1771
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 7, p. 2620 - 2623

1H-Benzimidazol-5-ol(41292-65-3)Related Product Information

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• TIMTEC-BB SBB005587
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