5-Bromo-1H-benzimidazole Chemical Properties

Melting point:

130 °C

Boiling point:

417.4±18.0 °C(Predicted)

Density 

1.770±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

11.19±0.30(Predicted)

color 

White to Yellow to Orange

InChI

InChI=1S/C7H5BrN2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,(H,9,10)

InChIKey

GEDVWGDBMPJNEV-UHFFFAOYSA-N

SMILES

C1NC2=CC(Br)=CC=C2N=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-36-22

Safety Statements 

22-26-36/37/39

WGK Germany 

3

HS Code 

2933998090

5-Bromo-1H-benzimidazole Usage And Synthesis

Chemical Properties

off-white powder

Uses

5-Bromo-1H-benzimidazole is a key intermediate in the synthesis of various organic compounds, especially in the fields of medicine and chemical research.

Synthesis

Step 87a: Synthesis of tert-butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate (compound 0601-187) To a solution of 4-bromo-1,2-benzenediamine (3 g, 16 mmol) in N,N-dimethylformamide (DMF, 22 mL) was added trimethyl orthoformate (44 mL), which was subsequently concentrated. Concentrated hydrochloric acid (1.5 mL) was added and the reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was diluted with deionized water (200 mL) and the pH was adjusted to 7 with saturated aqueous sodium bicarbonate. the reaction mixture was extracted with ethyl acetate (200 mL) and the organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 5-bromo-1H-benzo[d]imidazole (3.25 g, 100%) as an off-white solid. lc-MS (mass spectrum): m/z 197 [M + H]+. 1H NMR (400 MHz, DMSO-d6) δ 7.33 (t, J = 8.8 Hz, 1H), 7.55 (dd, J1 = 7.6 Hz, J2 = 40 Hz, 1H), 7.79 (d, J = 47.2 Hz, 1H), 8.26 (s, 1H), 12.61 (d, J = 25.6 Hz, 1H ).

References

[1] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 228
[2] Patent: US2013/102595, 2013, A1. Location in patent: Paragraph 0580; 0581
[3] Patent: JP2015/187145, 2015, A. Location in patent: Paragraph 0493
[4] Patent: US2009/326029, 2009, A1. Location in patent: Page/Page column 33

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