1337877-59-4

Basic information

• Product Name: 2,5-bis(4-methylphenyl)-3-hexylthiophene
• Synonyms: 2,5-bis(4-methylphenyl)-3-hexylthiophene
• CAS NO: 1337877-59-4
• Molecular Weight: 348.552
• Mol File: 1337877-59-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,5-bis(4-methylphenyl)-3-hexylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(4-methylphenyl)-3-hexylthiophene(1337877-59-4)
• EPA Substance Registry System: 2,5-bis(4-methylphenyl)-3-hexylthiophene(1337877-59-4)

Safety Data

• Hazardous Substances Data: 1337877-59-4(Hazardous Substances Data)

Upstream product

• 1693-86-3 3-hexylthiophene 
• 624-31-7 4-tolyl iodide 
• 5720-05-8 4-methylphenylboronic acid 
• 116971-11-0 2,5-dibromo-3-hexylthiophene 
• 106-38-7 para-bromotoluene 
• 51934-41-9 4-iodobenzoic acid ethyl ester 

Relevant articles and documents

Efficient double Suzuki cross-coupling reactions of 2,5-dibromo-3-hexylthiophene: Anti-Tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies

The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3a-i) synthesized via a Pd(0)-catalyzed Suzuki cross-coupling reaction in moderate to good yields. The novel compounds were also analyzed for their anti-thrombolytic, haemolytic, and biofilm inhibition activities. In addition, the anti-tumor activity was also evaluated in vitro for newly-synthesized compounds, where 3-hexyl-2,5-bis(4-(methylthio)phenyl)thiophene exhibited the best anti-tumor activity against 4T1 cells with IC50 value of 16 μM. Moreover, 2,5-bis(4-methylphenyl)-3-hexylthiophene showed the highest activity against MCF-7 cells with an IC50 value of 26.2 μM. On the other hand, the compound 2,5-bis(4-chloropheny)-3-hexylthiophene exhibited excellent biofilm inhibition activity. Furthermore, the compound 2,5-bis(3-chloro-4-fluorophenyl)-3-hexylthiophene also exhibited better anti-thrombolytic and hemolytic activity results as compared to the other newly-synthesized compounds.

Synthesis of well-defined head-to-tail-type oligothiophenes by regioselective deprotonation of 3-substituted thiophenes and nickel-catalyzed cross-coupling reaction

Iterative growth of thiophene oligomers by single-step extensions has been realized by regioselective metalation of 3-substituted thiophenes with the Knochel-Hauser base (TMPMgCl·LiCl) and coupling with bromothiophene using a nickel catalyst. Treatment of 3-hexylthiophene with TMPMgCl·LiCl induces metalation at the 5-position selectively. Subsequent addition of 2-bromo-3-hexylthiophene and a nickel catalyst leads to the corresponding bithiophene. The obtained bithiophene is converted to the terthiophene and then to the quaterthiophene by repeating the similar protocol. A concise synthesis of MK-1 and MK-2, which are organic dye molecules bearing an oligothiophene moiety that are used in photovoltaic cells, has been achieved.