5-Bromo-1-methyl-1H-benzo[d]imidazole Chemical Properties

Boiling point:

317.2±34.0 °C(Predicted)

Density 

1.60

storage temp. 

Sealed in dry,Room Temperature

pka

4.56±0.10(Predicted)

Appearance

Light brown to orange Solid

InChI

InChI=1S/C8H7BrN2/c1-11-5-10-7-4-6(9)2-3-8(7)11/h2-5H,1H3

InChIKey

KMJMDIYGNFGEEO-UHFFFAOYSA-N

SMILES

C1N(C)C2=CC=C(Br)C=C2N=1

5-Bromo-1-methyl-1H-benzo[d]imidazole Usage And Synthesis

Synthesis

To a solution of triethyl orthoformate (10 mL) of 4-bromo-N'-methylbenzene-1,2-diamine (1.7 g, 8 mmol) was added p-toluenesulfonic acid monohydrate (PTSA-H2O, 152 mg, 0.8 mmol). The reaction mixture was stirred at 85 °C for 2 hours. After completion of the reaction, the mixture was poured into water (50 mL) and extracted with ethyl acetate (EA, 40 mL × 2). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 50/1 to 10/1) to afford 5-bromo-1-methyl-1H-benzo[d]imidazole (1.5 g, 89% yield) as a yellow solid.LC-MS m/z: 211.1 [M + H]+. Retention time (tR) = 1.90 min.

References

[1] Patent: WO2017/176960, 2017, A1. Location in patent: Paragraph 00744
[2] Patent: WO2003/99776, 2003, A1. Location in patent: Page 34-35

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