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 Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

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(84946-20-3)Related Product Information

• 2-Chlorobenzimidazole
• Methyl salicylate
• Benzyl chloride
• 2-Chloromethylbenzimidazole
• Methyl acrylate
• Methanol
• Methylparaben
• Kresoxim-methyl
• Benzyl chloromethyl ether
• Benzimidazole
• METSULFURON METHYL
• Basic Violet 1
• Tribenuron methyl
• Mizolastine Impurity 8
• Mizolastine Impurity 3 Acetate
• Mizolastine Impurity 9
• 1-[1-(4-Fluorobenzyl)-1H-BenziMidazole-2yl]-N-Methyl-4-piperidineaMine
• Mizolastine Impurity 5