Home Chemistry Heterocyclic Building Blocks Thiophenes Benzo[1,2-B:4,5-B']Dithiophene
Electrophilic Aromatic Substitution: BDT contains an aromatic ring, and it can undergo electrophilic aromatic substitution reactions. For example, you can introduce substituents onto the BDT ring by treating it with electrophilic reagents such as acyl chlorides or bromine.
Reductive Coupling: BDT can undergo reductive coupling reactions to form dimers or oligomers. For instance, when treated with reducing agents or strong bases, BDT molecules can be coupled together, creating longer conjugated systems.
Oxidation: BDT is susceptible to oxidation reactions, especially at its sulfur atoms. Oxidizing agents can convert the sulfur atoms into sulfone or sulfoxide groups, depending on the reaction conditions.
Cross-Coupling Reactions: BDT can be used as a building block in various cross-coupling reactions, such as Suzuki-Miyaura, Stille, or Negishi couplings, to form more complex organic molecules.
Polymerization: BDT can be polymerized with other monomers, particularly electron-rich aromatic compounds like thiophene or EDOT (ethylene dioxythiophene), to create conjugated polymers. These polymers are often used in organic electronics and can exhibit semiconducting properties.
Halogenation: BDT can be halogenated at its aromatic ring, typically with chlorine or bromine, to introduce halogen substituents. This can be useful for further functionalization or for tuning the electronic properties of the compound.
Thiol Reactions: Due to its sulfur atoms, BDT can undergo reactions with thiol compounds to form thioether linkages. This type of reaction is commonly used in the synthesis of organic materials.
Catalytic Transformations: Various catalytic reactions can be employed to modify BDT, such as palladium-catalyzed cross-coupling reactions or transition-metal-catalyzed C-H activation reactions.
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4,8-Bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene
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2,6-Dibromo-4,8-dihexylbenzo[1,2-b:4,5-b']dithiophene
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Benzo[1,2-b:4,5-b']dithiophene-2,6-dicarbaldehyde
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4,8-Bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b']dithiophene
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(4,8-Bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane)
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Benzo[1,2-b:4,5-b']dithiophene-4,8-diyl bis(trifluoromethanesulfonate)
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2-Bromo-4,8-bis((2-octyldodecyl)oxy)benzo[1,2-b:4,5-b']dithiophene
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