5-Chloro-2-chloromethyl-1H-benzoimidazole

Basic information

Chinese name: 5-chloro-2-chloromethyl-1H-benzimidazole

CAS number: 15988-11-1

Molecular formula: C₈H₆Cl₂N₂

Molecular weight: 201.05 g/mol

Structural features: With the benzimidazole ring as the core, the 5-position is connected to a chlorine atom (-Cl), and the 2-position is connected to a chloromethyl group (-CH₂Cl). It is a chlorine-substituted benzimidazole derivative. The molecule contains two active chlorine atoms and a basic imidazole ring, and has active chemical properties.

Physical and chemical properties

Appearance and properties: Usually white to off-white crystalline powder, which may be light yellow when the purity is low; no special odor, good stability.

Melting point: about 158-162℃ (different purities may vary slightly).

Boiling point: not clearly reported, heating to above the melting point at normal pressure may decompose, generally purified by column chromatography or recrystallization.

Solubility: slightly soluble in water, easily soluble in polar organic solvents (such as methanol, ethanol, dichloromethane, ethyl acetate, DMF), and low solubility in non-polar solvents (such as n-hexane, ether).

Chemical properties:

The chlorine atom in the chloromethyl group (-CH₂Cl) at the 2nd position has nucleophilic substitution activity and can react with nucleophilic reagents such as amines, alcohols, and thiols to generate corresponding aminomethyl, ethermethyl, and thioethermethyl derivatives;

The chlorine atom at the 5th position is relatively stable, but can undergo substitution reactions under strong nucleophilic conditions (such as high temperature and strong base);

The N-H bond of the benzimidazole ring has a certain acidity and can react with strong bases to generate sodium salts or potassium salts, which further participate in alkylation reactions.