2-(4-Chlorobenzyl)benzimidazole Chemical Properties

Melting point:

197.3-198 °C

Boiling point:

479.7±28.0 °C(Predicted)

Density 

1.301±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.72±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C14H11ClN2/c15-11-7-5-10(6-8-11)9-14-16-12-3-1-2-4-13(12)17-14/h1-8H,9H2,(H,16,17)

InChIKey

COGUOPIIFAMLES-UHFFFAOYSA-N

SMILES

C1(CC2=CC=C(Cl)C=C2)NC2=CC=CC=C2N=1

CAS DataBase Reference

5468-66-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

37/39-26-36

HazardClass 

IRRITANT

MSDS

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2-(4-Chlorobenzyl)benzimidazole Usage And Synthesis

Chemical Properties

purple-pinkish crystalline powder

Synthesis

The general procedure for the synthesis of 2-(4-chlorobenzyl)benzimidazole from 4-chlorophenylacetic acid and o-phenylenediamine was as follows: 4-chlorophenylacetic acid (101.8 mmol) and sodium benzoate (0.37 mg, 0.46 mmol) were added to a 50 mL reaction flask fitted with a mechanical stirrer, a thermometer, a water separator and a reflux condenser. The reaction mixture was heated to 110 °C, followed by the addition of o-phenylenediamine (10 g, 92.5 mmol) and the temperature was raised to 120 °C and maintained for 1 hour. The course and endpoint of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent: ethyl acetate to petroleum ether in a volume ratio of 1:1, Rf=0.41). Upon completion of the reaction, the reaction mixture was neutralized with 5% by weight NaOH solution to pH 7.0 to 8.5. The resulting precipitate was filtered and washed with water to neutrality to give the crude product. The crude product was recrystallized with a mixed ethanol-water solvent (1:2 to 1:3, v/v), filtered and dried to give 21.3 g of pure 2-(4-chlorobenzyl)benzimidazole.

References

[1] Patent: CN103483266, 2016, B. Location in patent: Paragraph 0054; 0055; 0056
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 8, p. 1872 - 1878
[3] Journal of the American Chemical Society, 1954, vol. 76, p. 1883,1886
[4] Pharmazie, 2003, vol. 58, # 5, p. 303 - 307

2-(4-Chlorobenzyl)benzimidazole(5468-66-6)Related Product Information

• 2-Methylbenzimidazole
• 2-GUANIDINOBENZIMIDAZOLE
• 2-Chloromethylbenzimidazole
• 2-Phenylbenzimidazole
• Benzimidazole
• Benzyl chloromethyl ether
• 2-(Cyanomethyl)benzimidazole
• 5-Nitrobenzimidazole
• Benzyl chloride
• Clonitazene
• 2-(3,4-Dichlorobenzyl)-1H-benzimidazole
• 2-Methyl-1-(p-Chlorobenzyl)benzimidazole
• 1H-Benzimidazole,2-[(2,4-dichlorophenyl)methyl]-
• 2-(4-Chlorobenzyl)benzimidazole
• Alkyl benzimidazole
• benzimidazolone
• 3-[2-(4-CHLORO-BENZYL)-BENZOIMIDAZOL-1-YL]-PROPIONIC ACID
• 2-[2-(4-CHLOROBENZYL)-1H-BENZIMIDAZOL-1-YL]ETHANOL