3-Thiopheneacetic acid

3-Thiopheneacetic acid can be obtained from 3-thiopheneacetonitrile by strong base hydrolysis.

1.0 g (8.1 mmol) of 3-thiopheneacetonitrile was dissolved in 40-60 mL of an EtOH/H2O mixture (1:1), and about 10 times the excess of solid KOH was added. The mixture was then heated to 90 °C. After 3 hours, the ethanol was distilled off under reduced pressure, and the aqueous residue was diluted to 100 mL and extracted with CH2Cl2 (3×50 mL). Subsequently, the aqueous phase was set to pH 4-5 with 2N HCl. The acidified aqueous phase was extracted again with CH2Cl2 (3×50 mL).

The organic phase was dried over Na₂SO₄ and evaporated to dryness, yield: 1.1 g (94% of theoretical value), beige amorphous solid, mp 74-76℃ (decomposes).

white to light yellow crystal powder

3-Thiopheneacetic acid was used in:

• one-step, size control synthesis of gold nanoparticles
• in the preparation of gold nanoparticles capped with 3-thiopheneacetic acid (3-TAA) via borohydride reduction

3-Thiopheneacetic acid was used in one-step, size control synthesis of gold nanoparticles. It was also used in the preparation of gold nanoparticles capped with 3-thiopheneacetic acid (3-TAA) via borohydride reduction.

3-Thiopheneacetic acid acts as monocarboxylate ligand and forms oxo-carboxylate bridged digadolinium(III) complexes. Electrochemical oxidation of 3-thiopheneacetic acid in dry acetonitrile leads to the formation of a conducting polymeric film of poly (3-thiopheneacetic acid).

Crystallise the acid from ligroin or H2O. [Beilstein 18 III/IV 4066.]