2-(CHLOROMETHYL)-1-METHYL-1H-IMIDAZOLE HYDROCHLORIDE Chemical Properties

Melting point:

175 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder

color 

Beige

Safety Information

HS Code 

2933299090

2-(CHLOROMETHYL)-1-METHYL-1H-IMIDAZOLE HYDROCHLORIDE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (BB7) from 1-methyl-2-hydroxymethyl-1H-imidazole (BB6): to a solution of BB6 (35.5 g, 316.96 mmol) in dichloromethane (DCM, 1500 mL) was slowly added thionyl chloride (SOCl2, 330 mL, 4436 mmol ). The reaction mixture was gradually warmed to room temperature and stirred continuously for 5 hours. Upon completion of the reaction, the mixture was concentrated to remove the solvent. The residue was washed sequentially with dichloromethane (DCM, 2 × 500 mL) and ether (Et2O, 2 × 200 mL) to give the final target product BB7 (50 g, 95% yield) as an off-white solid. Thin-layer chromatography (TLC) showed an Rf value of 0.4 (unfolding agent: ethyl acetate).1H NMR (400 MHz, DMSO-d6) data were as follows: δ 7.76 (1H, apparent double peaks), 7.70 (1H, apparent double peaks), 5.17 (2H, single peak), 3.87 (3H, single peak); mass spectrometry (MS) showed an m/z of 131 ([M+H]+ ).

References

[1] Patent: US2012/322722, 2012, A1
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5308 - 5310
[3] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 19, p. 2291 - 2302
[5] Tetrahedron Letters, 2013, vol. 54, # 45, p. 6087 - 6089

2-(CHLOROMETHYL)-1-METHYL-1H-IMIDAZOLE HYDROCHLORIDE(78667-04-6)Related Product Information

• 2-(CHLOROMETHYL)-1-METHYL-1H-IMIDAZOLE HYDROCHLORIDE
• 1-BENZYL-2-(CHLOROMETHYL)-1H-IMIDAZOLE HCL
• 3-METHYLUNDECANE
• 2-(CHLOROMETHYL)-1-METHYL-1H-IMIDAZOLE
• IMIDAZOLE HYDROCHLORIDE
• 8-CHLORO-2-CHLOROMETHYL-6-TRIFLUOROMETHYL-IMIDAZO[1,2-A]PYRIDINE
• 1-BENZYL-2-CHLOROMETHYL-1H-BENZOIMIDAZOLE HYDROCHLORIDE
• 8-CHLORO-2-(CHLOROMETHYL)IMIDAZO[1,2-A]PYRIDINE
• 6,8-DICHLORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBALDEHYDE
• ethyl 6,8-dichloroimidazo[1,2-a]pyridine-2-carboxylate
• 5-CHLORO-2-(CHLOROMETHYL)-1-METHYL-1H-IMIDAZOLE HYDROCHLORIDE
• 5-(Chloromethyl)-4-methyl-1H-imidazole hydrochloride
• 2-[6-CHLORO-2-(CHLOROMETHYL)-1H-BENZIMIDAZOL-1-YL]ETHANOL
• [4-(6,8-DICHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-THIAZOL-2-YL]-HYDRAZINE
• 1-(4-CHLOROBENZYL)-2-(CHLOROMETHYL)-1H-IMIDAZOLE HYDROCHLORIDE
• 2-(1,3-BENZODIOXOL-5-YL)-3,8-DICHLORO-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE
• 8-CHLORO-2-(3,4-DICHLOROPHENYL)-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE
• 6,8-dichloro-2-(chloromethyl)imidazo[1,2-a]pyridine