2-AMINO-4-TRIFLUOROMETHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER Chemical Properties

Melting point:

170 °C

Boiling point:

81.4°C (rough estimate)

Density 

1.479

storage temp. 

2-8°C, protect from light

pka

0.08±0.10(Predicted)

Appearance

White to light yellow Solid

CAS DataBase Reference

344-72-9(CAS DataBase Reference)

EPA Substance Registry System

5-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl ester (344-72-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2934100090

Toxicity

LDLo ivn-mus: 75 mg/kg CBCCT* 6,142,54

2-AMINO-4-TRIFLUOROMETHYL-THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 28, p. 907, 1991 DOI: 10.1002/jhet.5570280412

Safety Profile

Poison by intravenous route.When heated to decomposition it emits toxic vapors ofNOx and SOx.

Synthesis

Step 1: Synthesis of ethyl 2-amino-4-trifluoromethylthiazole-5-carboxylate (A-31) To an ethanol (200 mL) suspension of thiourea (3.3 g, 22.88 mmol) was added ethyl 2-chloro-4,4,4-trifluoroacetoacetate (5 g, 22.88 mmol), and the resulting reaction mixture was heated at 80 °C for 24 hours. Subsequently, the reaction mixture was cooled to room temperature and concentrated under vacuum. The crude product was purified by column chromatography to afford ethyl 2-amino-4-trifluoromethylthiazole-5-carboxylate (A-31) as a colorless oil (5.98 g, 85% yield). 1H NMR (500 MHz, CDCl3) δ 4.32 (q, 2H, J = 7.0 Hz), 3.56 (m, 4H), 1.70 (m, 6H), 1.36 (t, 3H, J = 7.0 Hz); LCMS (ESI) [M + 1]+ 309.3.

References

[1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3395 - 3402
[2] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1625 - 1629
[3] Patent: WO2010/59606, 2010, A2. Location in patent: Page/Page column 169
[4] Tetrahedron Letters, 2005, vol. 46, # 13, p. 2251 - 2252
[5] Patent: US2004/138268, 2004, A1. Location in patent: Page/Page column 15

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