4-TRIFLUOROMETHYL-THIAZOL-2-YLAMINE Chemical Properties

Melting point:

60-62°C

Boiling point:

125-128 °C(Press: 22 Torr)

Density 

1.557±0.06 g/cm3(Predicted)

storage temp. 

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

form 

crystalline solid

pka

1.90±0.10(Predicted)

color 

Yellow

InChI

InChI=1S/C4H3F3N2S/c5-4(6,7)2-1-10-3(8)9-2/h1H,(H2,8,9)

InChIKey

OVMGTNMCYLZGLS-UHFFFAOYSA-N

SMILES

S1C=C(C(F)(F)F)N=C1N

CAS DataBase Reference

349-49-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-43-36

Safety Statements 

26-36/37/39-36/37

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934100090

4-TRIFLUOROMETHYL-THIAZOL-2-YLAMINE Usage And Synthesis

Uses

4-(Trifluoromethyl)-2-thiazolamine can be used to prepare phenethylthiazolylthiourea analogs as HIV-1 reverse transcriptase inhibitors. 4-(Trifluoromethyl)-2-thiazolamine can also be used to synthesize 2-amino benzamide derivatives as allosteric glucokinase activators.

Synthesis

General procedure for the synthesis of 2-amino-4-trifluoromethylthiazole from 3-bromo-1,1,1-trifluoroacetone and thiourea: Thiourea (4.0 g, 52.3 mmol) and 3-bromo-1,1,1-trifluoropropan-2-one (5.5 mL, 10 g, 52.3 mmol) were added to ethanol (100 mL) and the reaction was heated for 2 hours at 50 °C. After completion of the reaction, it was cooled to room temperature and the reaction solution was concentrated to dryness. The residue was dissolved in water and the pH was adjusted with 2 M NaOH solution to >12. Subsequently, four extractions were performed with ether. The organic extracts were combined, dried with sodium sulfate, filtered and concentrated in vacuum. The resulting crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to afford 2-amino-4-trifluoromethylthiazole (6.9 g, 79% yield). es/MS m/z 169 (M + 1)+.

References

[1] Patent: WO2008/36579, 2008, A1. Location in patent: Page/Page column 43
[2] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 907 - 911
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1051 - 1053
[4] Journal of Organic Chemistry, 1955, vol. 20, p. 499,505
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2335 - 2339

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