Description
2,5-Dibromo-3-cyclohexylthiophene (CAS No. 302912-44-3) is a high-purity brominated thiophene derivative with the molecular formula C10H12Br2S. This organosulfur compound features a cyclohexyl substituent at the 3-position and bromine atoms at the 2- and 5-positions of the thiophene ring, making it a versatile intermediate for organic synthesis and materials science applications. With a molecular weight of 316.07 g/mol, it is supplied as a crystalline solid with ≥97% purity (HPLC), ensuring consistency for demanding research applications. Ideal for use in cross-coupling reactions (e.g., Suzuki, Stille), this compound serves as a key precursor for conjugated polymers, organic semiconductors, and liquid crystals. Store under inert atmosphere at 2-8°C to maintain stability. Hazard statements apply – consult SDS for safety protocols.
Properties
- CAS Number: 302912-44-3
- Complexity: 168
- IUPAC Name: 2,5-dibromo-3-cyclohexyl-thiophene
- InChI: InChI=1S/C10H12Br2S/c11-9-6-8(10(12)13-9)7-4-2-1-3-5-7/h6-7H,1-5H2
- InChI Key: GQDHHQWPBULMEB-UHFFFAOYSA-N
- Exact Mass: 323.90060
- Molecular Formula: C10H12Br2S
- Molecular Weight: 324.08
- SMILES: C1CCC(CC1)C2=C(SC(=C2)Br)Br
- Topological: 28.2
- Monoisotopic Mass: 321.90265
- Synonyms: 2,5-Dibromo-3-cyclohexylthiophene, 302912-44-3, 2 5-DIBROMO-3-CYCLOHEXYLTHIOPHENE 97, 2 5-DIBROMO-3-CYCLOHEXYLTHIOPHENE97, MFCD02683539, SCHEMBL197004, DTXSID50391617, 2,5-Dibromo-3-cyclohexylthiophene, 97%, CS-0106560, D5247, T70732
Application
2,5-Dibromo-3-cyclohexylthiophene is widely employed as a monomer in the synthesis of π-conjugated polymers for organic electronics, including OFETs and OLEDs. Its dibromo functionality enables efficient palladium-catalyzed polymerization, while the cyclohexyl group enhances solubility in organic solvents. Researchers utilize this compound to modify the bandgap and charge transport properties of polythiophenes. It also serves as a building block for small-molecule semiconductors in photovoltaic applications.
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