Chemical Properties
Colorless liquid
Uses
3-Thiophenemethanol was used in the preparation of 3-substituted thiophene conducting copolymers which has potential applications in electrochromic displays. It was also used in the synthesis of 4-(thiophene-3-ylmethoxy)phthalonitrile.
Definition
ChEBI: 3-Thiophenemethanol is a heteroarene.
General Description
Comparision of electrochemical polymerization properties of 3-thiophenemethanol and 3-methylthiophene has been reported.
Synthesis
The general procedure for the synthesis of 3-thiophene methanol from 3-bromothiophene-4-carboxaldehyde was as follows: 3-bromothiophene-4-carboxaldehyde (930 mg, 5.0 mmol), sodium acetate (820 mg, 10.0 mmol), methanol (30 mL), and palladium chloride (45 mg) were mixed in a balloon-covered glass vial filled with hydrogen. The reaction mixture was stirred at 35 °C for 4 h before being filtered and washed with methanol. Subsequently, the solvent was removed by reduced pressure distillation and the residue was dissolved in water, neutralized with solid sodium bicarbonate and extracted with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate and filtered. Finally, the solvent was removed by reduced pressure distillation and the residue was purified by column chromatography to give 3-thiophene methanol (428 mg, 78% yield).
References
[1] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3798 - 3801
