1H-Benzimidazole,5,6-difluoro-(9CI)

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1H-Benzimidazole,5,6-difluoro-(9CI) Basic information
Product Name:1H-Benzimidazole,5,6-difluoro-(9CI)
Synonyms:1H-Benzimidazole,5,6-difluoro-(9CI);5,6-difluoro-1H-benzo[d]iMidazole;1H-Benzimidazole,5,6-difluoro-
CAS:78581-99-4
MF:C7H4F2N2
MW:154.12
EINECS:
Product Categories:BENZIMIDAZOLE
Mol File:78581-99-4.mol
1H-Benzimidazole,5,6-difluoro-(9CI) Structure
1H-Benzimidazole,5,6-difluoro-(9CI) Chemical Properties
Melting point 159-161°
Boiling point 369.5±22.0 °C(Predicted)
density 1.488±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka11.54±0.30(Predicted)
AppearancePurple to light brown Solid
Safety Information
HS Code 2933998090
MSDS Information
1H-Benzimidazole,5,6-difluoro-(9CI) Usage And Synthesis
Synthesis
Formic acid

64-18-6

1,2-DIAMINO-4,5-DIFLUOROBENZENE

76179-40-3

1H-Benzimidazole,5,6-difluoro-(9CI)

78581-99-4

The general procedure for the synthesis of 5,6-difluorobenzimidazole from 4,5-difluorophthalimide and formic acid was as follows: 4,5-difluorophthalimide (1.5 g, 10 mmol) was dissolved in formic acid (20 mL) and the reaction was heated for 12 hr at 80 °C. Upon completion of the reaction, the mixture was cooled to 25 °C and subsequently concentrated under reduced pressure to remove the solvent. The resulting residue was purified by recrystallization from a solvent mixture of petroleum ether and ethyl acetate (15:1, v/v) to give the final yellow solid 5,6-difluoro-1H-benzo[d]imidazole (1.4 g, 88% yield). Mass spectrum (ESI) m/z: 155 [M + H]+.

References[1] Patent: WO2015/100609, 2015, A1. Location in patent: Page/Page column 45
[2] Patent: EP2766359, 2016, B1. Location in patent: Paragraph 0756
[3] New Journal of Chemistry, 2006, vol. 30, # 5, p. 803 - 809
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 14, p. 3674 - 3678
[5] ChemCatChem, 2018, vol. 10, # 19, p. 4338 - 4345
1H-Benzimidazole,5,6-difluoro-(9CI) Preparation Products And Raw materials
Raw materialsFormic acid-->1,2-Diamino-4,5-difluorobenzene-->N,N-Dimethylformamide
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