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| | 1-(4-Fluorobenzyl)-2-chlorobenzimidazole Basic information |
| | 1-(4-Fluorobenzyl)-2-chlorobenzimidazole Chemical Properties |
| Melting point | 83-87 °C(lit.) | | Boiling point | 432.3±47.0 °C(Predicted) | | density | 1.30±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,2-8°C | | solubility | soluble in Methanol | | form | powder to crystal | | pka | 3.42±0.10(Predicted) | | color | White to Almost white | | InChI | InChI=1S/C14H10ClFN2/c15-14-17-12-3-1-2-4-13(12)18(14)9-10-5-7-11(16)8-6-10/h1-8H,9H2 | | InChIKey | PGXALMVNIRPELS-UHFFFAOYSA-N | | SMILES | C1(Cl)N(CC2=CC=C(F)C=C2)C2=CC=CC=C2N=1 | | CAS DataBase Reference | 84946-20-3(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | HS Code | 2933998090 | | Storage Class | 13 - Non Combustible Solids |
| | 1-(4-Fluorobenzyl)-2-chlorobenzimidazole Usage And Synthesis |
| Chemical Properties | White Solid | | Uses | A novel aldose reductase (ALR2) inhibitor. | | Synthesis | General procedure for the synthesis of 1-(4-fluorobenzyl)-2-chlorobenzimidazole from 2-chlorobenzimidazole and 4-fluorobenzyl bromide: To a solution of 2-chlorobenzimidazole (5 g, 32.7 mmol) in acetonitrile (30 ml) was added potassium hydroxide (2.62 g, 46.6 mmol). The mixture was heated to 80°C and stirred for 30 minutes until the solution was clarified. After cooling to room temperature, 4-fluorobenzyl bromide (9.29 g, 49.1 mmol) was added and the reaction was refluxed at 80 °C for 5 h. The reaction solution appeared white and turbid. After completion of the reaction, the reaction solution was extracted with dichloromethane (100 mL x 3) three times, the organic layers were combined, washed with distilled water and dried with anhydrous magnesium sulfate. After filtration, the organic phase was concentrated to give a white solid. It was recrystallized by acetone/petroleum ether mixed solvent, cooled, filtered and dried to obtain a white solid product in 91.1% yield. | | References | [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 3, p. 245 - 249
[2] Patent: CN104910894, 2017, B. Location in patent: Paragraph 0032; 0034; 0036; 0037; 0055
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 25, p. 6291 - 6294
[4] Heterocycles, 1999, vol. 51, # 11, p. 2561 - 2573
[5] Patent: US5922737, 1999, A |
| | 1-(4-Fluorobenzyl)-2-chlorobenzimidazole Preparation Products And Raw materials |
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