Description
2,5-Dibromo-3-octadecylthiophene (CAS No. 205235-01-4) is a high-purity brominated thiophene derivative with the molecular formula C22H38Br2S. This compound features a long octadecyl (C18) alkyl chain attached to the 3-position of the thiophene ring, along with bromine substituents at the 2- and 5-positions, making it a valuable intermediate for organic synthesis and materials science applications. Its hydrophobic alkyl chain enhances solubility in non-polar solvents, while the bromine atoms provide reactive sites for further functionalization via cross-coupling reactions such as Suzuki or Stille couplings. Ideal for researchers developing conjugated polymers, organic semiconductors, or liquid crystalline materials, this product is rigorously tested for purity and consistency. Available in quantities ranging from milligrams to bulk scales, it is packaged under inert conditions to ensure stability.
Properties
- CAS Number: 205235-01-4
- Complexity: 285
- IUPAC Name: 2,5-dibromo-3-octadecyl-thiophene
- InChI: InChI=1S/C22H38Br2S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-19-21(23)25-22(20)24/h19H,2-18H2,1H3
- InChI Key: ZKEZVCBCCSWUTA-UHFFFAOYSA-N
- Exact Mass: 494.10405
- Molecular Formula: C22H38Br2S
- Molecular Weight: 494.4
- SMILES: CCCCCCCCCCCCCCCCCCC1=C(SC(=C1)Br)Br
- Topological: 28.2
- Monoisotopic Mass: 492.10610
- Synonyms: 2,5-Dibromo-3-octadecylthiophene, 205235-01-4, MFCD29086861, D5243, D90377
Application
2,5-Dibromo-3-octadecylthiophene is widely used in the synthesis of conjugated polymers for organic electronics, including organic field-effect transistors (OFETs) and photovoltaic devices. Its brominated thiophene core serves as a key monomer for polymerization via metal-catalyzed cross-coupling reactions. The long alkyl chain improves processability and film-forming properties in thin-film applications. Researchers also utilize this compound to study self-assembly and charge transport in supramolecular systems.
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