ETHYL 2-(BROMOMETHYL)-1,3-THIAZOLE-4-CARBOXYLATE Chemical Properties

Boiling point:

290.8±20.0 °C(Predicted)

Density 

1.602±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

-0.45±0.10(Predicted)

ETHYL 2-(BROMOMETHYL)-1,3-THIAZOLE-4-CARBOXYLATE Usage And Synthesis

Uses

2-Bromomethyl-4-carboxylic acid ethyl thiazole is a monobrominated methylthiazole derivative with good reactivity and is often used as a substructure for pre-molecular modification of drugs.

Synthesis

General procedure for the synthesis of ethyl 2-(bromomethyl)thiazole-4-carboxylate from ethyl 2-methylthiazole-4-carboxylate: ethyl 2-methyl-1,3-thiazole-4-carboxylate (500 mg, 2.92 mmol) was dissolved in carbon tetrachloride (10 mL), N-bromosuccinimide (NBS, 624 mg, 3.50 mmol) was added, and the reaction mixture was heated at 76 °C for 60 min. Subsequently, azobisisobutyronitrile (AIBN, 36 mg, 0.21 mmol) was added and heating was continued at 76 °C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through diatomaceous earth. The filter cake was washed with dichloromethane (DCM). The organic layers were combined, concentrated in vacuum through a silica column and purified using fast column chromatography (FCC) with a heptane solution of 50% ethyl acetate (EtOAc) as eluent to give the final ethyl 2-(bromomethyl)thiazole-4-carboxylate. Yield: 274 mg in 38% yield.

References

[1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 1 - 6
[2] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 156
[3] Patent: US2006/122256, 2006, A1. Location in patent: Page/Page column 21
[4] Patent: US2004/266856, 2004, A1. Location in patent: Page/Page column 19
[5] Liebigs Annalen der Chemie, 1981, # 4, p. 623 - 632

ETHYL 2-(BROMOMETHYL)-1,3-THIAZOLE-4-CARBOXYLATE(78502-71-3)Related Product Information

• Sulfathiazole
• 2-Bromomethylthiazole
• ETHYL 2-(BROMOMETHYL)-1,3-THIAZOLE-4-CARBOXYLATE