Ethyl 2-aminothiazole-5-carboxylate Chemical Properties

Melting point:

144-148

Boiling point:

308.0±15.0 °C(Predicted)

Density 

1.336±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

Water Solubility 

Insoluble in water

form 

powder to crystal

pka

3.12±0.10(Predicted)

color 

White to Yellow to Orange

Sensitive 

Moisture & Light Sensitive

λmax

299nm(EtOH)(lit.)

InChI

InChI=1S/C6H8N2O2S/c1-2-10-5(9)4-3-8-6(7)11-4/h3H,2H2,1H3,(H2,7,8)

InChIKey

VNZXERIGKZNEKB-UHFFFAOYSA-N

SMILES

S1C(C(OCC)=O)=CN=C1N

CAS DataBase Reference

32955-21-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

2

HazardClass 

IRRITANT

HS Code 

29339900

Ethyl 2-aminothiazole-5-carboxylate Usage And Synthesis

Chemical Properties

White to yellow or light brown crystal or powder

Uses

2-Amino-5-thiazolecarboxylic Acid Ethyl Ester is used in the synthesis of dual-action antidiabetic agents that inhibit glycogen phosphorylase.

Synthesis Reference(s)

Tetrahedron Letters, 42, p. 2101, 2001 DOI: 10.1016/S0040-4039(01)00161-7

Synthesis

1. N-bromosuccinimide (19.6 g, 0.11 mol) was slowly added to a water/dioxane (1:1, 100 mL) solution of ethyl 3-ethoxyacrylate (14.4 g, 0.1 mol) at -10 °C. 2. The reaction mixture was stirred at room temperature for 1 h. 3. After the addition of thiourea (7.6 g, 0.1 mol), the reaction mixture was was heated to 80 °C and maintained for 1 h. 4. Upon completion of the reaction, the solution was cooled to room temperature followed by the addition of ammonia (20 mL). 5. The resulting paste was stirred at room temperature for 10 min and then filtered. 6. The filter cake was washed with water and dried under vacuum to give the final product, ethyl 2-aminothiazole-5-carboxylate (12.1 g, 70% yield).

References

[1] Patent: EP2615092, 2013, A1. Location in patent: Paragraph 0095; 0096
[2] Patent: WO2006/8556, 2006, A1. Location in patent: Page/Page column 20-21

Ethyl 2-aminothiazole-5-carboxylate(32955-21-8)Related Product Information

• 2-AMINODIETHYLMALONATE
• ISOXADIFEN-ETHYL
• RESMETHRIN
• Ethyl formate
• Benzocaine
• Ethyl acrylate
• Ethyl pyruvate
• 2-(2-Aminothiazol-4-yl)glyoxylic acid
• 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester
• Urethane
• Ethyl cyanoacetate
• ETHYL 3-AMINOCROTONATE
• 2-Aminothiazole
• Ethyl acetate
• Ethanol
• Ethylparaben
• ETHYL 2-AMINOTHIAZOLE-4-CARBOXYLATE
• Methyl 2-aminothiazole-5-carboxylate