2-Amino-4-chloromethythiazole hydrochloride Chemical Properties

Melting point:

141-143 °C(Solv: ethanol (64-17-5))

storage temp. 

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

form 

solid

Appearance

White to off-white Solid

CAS DataBase Reference

59608-97-8(CAS DataBase Reference)

EPA Substance Registry System

2-Thiazolamine, 4-(chloromethyl)-, monohydrochloride (59608-97-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

HazardClass 

IRRITANT

HS Code 

2934100090

2-Amino-4-chloromethythiazole hydrochloride Usage And Synthesis

Uses

2-Amino-4-chloromethyl thiazole hydrochloride is an α-thiophene derivative, which is widely used in synthetic medicines, pesticides, dyes, chemical reagents, polymer additives, etc.

Synthesis

The general procedure for the synthesis of 2-amino-4-chloromethylthiazole hydrochloride from the compound (CAS: 17356-08-0) and 1,3-dichloroacetone was carried out as follows: a mixture of 1,3-dichloroacetone (380.9 g, 3 mol), thiourea (228.3 g, 3 mol), and isopropanol (3.6 L) was stirred at 40 °C in an inert atmosphere until a clarified solution. Subsequently, the reaction mixture was continued to be stirred at room temperature overnight to induce crystallization of the product. Upon completion of the reaction, the mixture was cooled to -20 °C to promote complete crystallization and the product was subsequently isolated by filtration. The resulting crystals were washed with cold isopropanol (0.4 L) and finally dried under vacuum to afford 2-amino-4-chloromethylthiazole hydrochloride as white crystals (408 g, 73.5% yield).

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9686 - 9720
[2] Patent: WO2009/15193, 2009, A1. Location in patent: Page/Page column 44
[3] Bollettino Chimico Farmaceutico, 1995, vol. 134, # 11, p. 639 - 643
[4] Patent: WO2008/11191, 2008, A1. Location in patent: Page/Page column 36
[5] Patent: EP3018125, 2016, A1. Location in patent: Paragraph 0753-0755

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