Thiophene-2-ethylamine

Chemical properties

A colorless to yellow liquid with unstable properties requiring protection with nitrogen gas. It appears as a light yellow clear liquid, but turns red upon prolonged exposure.

The Uses of Thiophene-2-ethylamine

[2-(Thiophene-2-yl)ethyl]amine is used in the synthesis of geldanamycin derivatives as HCV replication inhibitors targetting Hsp90.

The Uses of Thiophene-2-ethylamine

2-Thiopheneethylamine (2-thiophene ethyl amine, 2-(thien-2-yl)ethylamine) is suitable to functionalize multiwall carbon nanotubes (MWCNT).
It may be used as a reactant in the synthesis of pyrimidine derivatives by reacting with various isothiocyanatoketones and acylguanidines derivatives by reacting with aroyl S-methylisothiourea.

General Description

2-Thiopheneethylamine (2-(thiophen-2-yl)ethanamine) is an aromatic amine. It undergoes microwave induced condensation with iminodiacetic acid to form the corresponding piperazine-2,6-dione derivatives. Its effect as a probable substitute to the pyridine ligand on the performance of poly(3-hexylthiophene)/CdSe hybrid solar cells has been investigated.

Synthesis

N,N-Dimethylformamide (DMF) reacts with thiophene to obtain 2-thiophenecarbaldehyde, then reacts with isopropyl chloroacetate to obtain 2-thiopheneacetaldehyde, and then reacts with hydroxylamine hydrochloride to obtain 2-thiopheneacetaldehyde oxime, and finally reduced to give 2-thiopheneethylamine.

References

[1] M. BARWIOLEK. Structural and spectral studies of silver(I) complexes with new Schiff bases derived from 2-thiopheneethylamine and their application in thin layer deposition by spin and dip coating techniques[J]. Polyhedron, 2017, 124: Pages 12-21. DOI:10.1016/j.poly.2016.12.011.
[2] BHUSHAN D. VARPE S B J. Schiff Base of Isatin with 2-Thiopheneethylamine and Its Mannich Bases: Synthesis, Docking, and In Vitro Anti-Inflammatory and Antitubercular Activity[J]. Russian Journal of Bioorganic Chemistry, 2022, 48 2: 372-379. DOI:10.1134/S1068162022020030.
[3] JUN YAN LEK. Understanding the Effect of Surface Chemistry on Charge Generation and Transport in Poly (3-hexylthiophene)/CdSe Hybrid Solar Cells[J]. ACS Applied Materials & Interfaces, 2011, 3 2: 287-292. DOI:10.1021/am100938f.
[4] SANDEEP KUMAR. Efficient synthesis of piperazine-2,6-dione and 4-(1H-indole-2-carbonyl)piperazine-2,6-dione derivatives and their evaluation for anticancer activity[J]. Medicinal Chemistry Research, 2013, 22 10: 4600-4609. DOI:10.1007/s00044-012-0438-7.