4-(Trifluoromethyl)-1H-imidazole Chemical Properties

Melting point:

149-150

Boiling point:

224.7±35.0 °C(Predicted)

Density 

1.440±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

10.29±0.10(Predicted)

form 

Solid

color 

White to Almost white

InChI

InChI=1S/C4H3F3N2/c5-4(6,7)3-1-8-2-9-3/h1-2H,(H,8,9)

InChIKey

DFLGRTIPTPCKPJ-UHFFFAOYSA-N

SMILES

C1NC(C(F)(F)F)=CN=1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38-40

Safety Statements 

26-36/37-24/25

Hazard Note 

Irritant

HS Code 

29349990

4-(Trifluoromethyl)-1H-imidazole Usage And Synthesis

Chemical Properties

Off-white crystalline powder

Uses

4-Trifluoromethyl-1H-imidazole acts as an inhibitor of sweet almond β-glucosidase. It is used as a reagent used in the synthesis of 3-substituted 2-aminopyridines via displacement of 3-fluoro-2-nitropyridine.

Synthesis

Procedure for the synthesis of 4-(trifluoromethyl)-1H-imidazole: 3-bromo-1,1,1-trifluoropropan-2-one (25.0 g, 131 mmol, Aldrich Item No. 374059) and formamide (104 mL, 2.62 mol) were sequentially added to a 500 mL round bottom flask. The reaction mixture was slowly heated to reflux temperature (about 140 °C) and kept at reflux for 2.5 hours of reaction. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with 200 mL of 10% aqueous K2CO3 solution and subsequently extracted with ether (5 x 200 mL). The organic phases were combined, washed sequentially with 10% aqueous K2CO3 (2 x 100 mL) and deionized water (2 x 100 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a brown solid. The resulting solid was washed with dichloromethane (DCM) to finalize 4-(trifluoromethyl)-1H-imidazole (4.0 g, 22% yield) as a brown solid. The structure of the product was confirmed by 1H NMR (CD3OD): δ 7.82 (s, 1H), 7.60 (s, 1H).

References

[1] Patent: WO2010/83246, 2010, A1. Location in patent: Page/Page column 100

4-(Trifluoromethyl)-1H-imidazole(33468-69-8)Related Product Information

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