2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLIC ACID Chemical Properties

Melting point:

158 °C (dec.)

Boiling point:

349.5±22.0 °C(Predicted)

Density 

1.895±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.16±0.37(Predicted)

color 

White to Light yellow to Light orange

CAS DataBase Reference

40003-41-6

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

WGK Germany 

3

HS Code 

2934100090

MSDS

• Language:English Provider:SigmaAldrich

2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLIC ACID Usage And Synthesis

Uses

2-Bromo-4-methyl-5-thiazolecarboxylic Acid, is a heterocyclic building block used for the preparation of various chemicals. It is used in the synthesis of new azole Antifungals.

Synthesis

General procedure for the synthesis of 2-bromo-4-methylthiazole-5-carboxylic acid from ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate: 5N aqueous NaOH solution (15 mL) was added to a solution of ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (1 mmol) in ethanol (20 mL), and the reaction mixture was stirred for 14 h at room temperature. The reaction progress was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled and neutralized with concentrated hydrochloric acid. The organic layer was extracted with ethyl acetate (EtOAc) and the organic phase was dried with anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by column chromatography using silica gel (60-120 mesh) as stationary phase and gradient elution with a mixed solvent of ethyl acetate and petroleum ether, which ultimately afforded 2-bromo-4-methylthiazole-5-carboxylic acid as an off-white solid in 76% yield. The structure of the product was confirmed by 1H NMR (CDCl3, δ: 13.19, s, 1H; 2.54, s, 3H) and mass spectrometry (ESI-MS, m/z: 223 [M+H]+).

References

[1] Patent: EP2604268, 2015, B1. Location in patent: Paragraph 0150-0151
[2] Russian Journal of General Chemistry, 2016, vol. 86, # 7, p. 1722 - 1729
[3] Zh. Obshch. Khim., 2016, vol. 86, # 7, p. 1722 - 1729,8
[4] Justus Liebigs Annalen der Chemie, 1890, vol. 259, p. 298
[5] Roczniki Chemii, 1972, vol. 46, p. 1647 - 1658

2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLIC ACID(40003-41-6)Related Product Information

• 2-Bromo-4-methylthiazole
• 4-Methylthiazole
• 4-Methylthiazole-5-carboxylic acid
• ETHYL 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE
• 2-BROMO-4-(TRIFLUOROMETHYL)THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER
• 5-Thiazolecarboxylicacid,2-bromo-4-methyl-,methylester(9CI)
• 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLIC ACID
• 2-Bromo-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid
• 5-Thiazolecarboxylicacid,2-bromo-4-(1,1-dimethylethyl)-,ethylester(9CI)