4-(4-FLUOROPHENYL)-1H-IMIDAZOLE Chemical Properties

Melting point:

124-129 °C

form 

solid

InChI

1S/C9H7FN2/c10-8-3-1-7(2-4-8)9-5-11-6-12-9/h1-6H,(H,11,12)

InChIKey

QYDAFWKRBZYBOB-UHFFFAOYSA-N

SMILES

Fc1ccc(cc1)-c2c[nH]cn2

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26

WGK Germany 

3

HS Code 

2933299090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Dam. 1

4-(4-FLUOROPHENYL)-1H-IMIDAZOLE Usage And Synthesis

Uses

4-(4-Fluorophenyl)-1H-imidazolium is an imidazolium heterocyclic derivative that can be used as an intermediate in pharmaceutical and chemical synthesis.

Synthesis

A mixture of 2-bromo-1-(4-fluorophenyl)ethanone (10.9 g, 50 mmol) and formamide (14 mL, 350 mmol) was stirred at 170 ??C and under nitrogen for 4 hours. The reaction mixture was cooled and mixed with ethyl acetate (40 mL). Saturated aqueous sodium bicarbonate (50 mL) was carefully added while the mixture was cooled in an ice water bath. The aqueous layer was separated and extracted with ethyl acetate (2 x 40mL). The combined organic solutions were washed with water (30 mL) and brine (30 mL), dried (Na2SO 4) and concentrated.  Rapid chromatography on silica gel (10-100% hexane solution of ethyl acetate) yielded 4-(4-fluorophenyl)-1H-imidazole (3.46 g, 21 mmol, 43% yield) as a solid.

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