• 3,3'-Dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene (CAS 207742-50-5) - TCI D3941 - AMI Scientific
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TCI

CAS 207742-50-5

3,3'-Dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene TCI D3941

3,3'-Dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene TCI D3941
Rp 3.807.300,00
Rp 3.807.300,00
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TCI D3941 3,3'-Dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene is a bithiophene building block developed specifically for materials chemistry, and in particular for the preparation of polymer semiconductors and conjugated macromolecules. The molecule is built around a core of two thiophene rings joined at the 2 and 2' positions, carrying bromine atoms at the 3 and 3' positions and trimethylsilyl groups at the 5 and 5' positions. This carefully arranged substitution pattern makes it a highly valuable starting material for researchers who need to construct fused aromatic frameworks with genuinely controlled reaction sites.

The property that leads researchers to select this compound is the presence of two distinct classes of functional group, each playing a different role. The bromine atoms at the 3 and 3' positions act as reactive handles for metal-catalysed cross-coupling reactions and for halogen–metal exchange, the key step in forming bridges between the rings. The trimethylsilyl groups at the 5 and 5' positions, meanwhile, work simultaneously as protecting groups and as blocking groups on the most reactive alpha positions, preventing reactions from occurring at unwanted sites. These silyl groups can then be removed or replaced at a later stage, giving a level of regiochemical control that is otherwise difficult to achieve.

In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic electronics and functional polymer materials. It suits synthetic work where a conjugated backbone must be assembled step by step, with the position of each new bond defined in advance. Because the reactive and protected sites are already differentiated within the molecule, research teams can plan multi-step routes with fewer separation problems and a more predictable outcome at each stage.

  • Polymer semiconductor synthesis: the differentiated bromine and trimethylsilyl positions allow a conjugated backbone to be extended in a defined direction rather than randomly.
  • Metal-catalysed cross-coupling reactions: the 3,3'-bromine atoms serve as ready reactive handles for coupling chemistry, giving controlled bridge formation between thiophene rings.
  • Halogen–metal exchange chemistry: the bromine substituents can be converted into organometallic intermediates, opening access to further functionalisation at precisely those two positions.
  • Fused aromatic framework construction: the fixed substitution pattern lets researchers build fused ring systems where every new bond is formed at a predetermined site.
  • Conjugated macromolecule research: the removable silyl groups protect the reactive alpha positions during assembly, then free them again for later modification of the macromolecule.

Brand TCI (Tokyo Chemical Industry)
CAS number 207742-50-5
Molecular formula —
Purity —
Category Materials Science > Material Building Blocks > Polymer/Macromolecule Semiconductor Building Blocks
Pack sizes available in the standard research-scale pack sizes offered by TCI for this catalogue item
Physical form —
Storage store according to the conditions stated on the manufacturer's label and safety data sheet
  • Product code: TCI D3941

Store the material in its original tightly closed container, in a cool, dry and well-ventilated area away from heat, direct sunlight, moisture and incompatible chemicals, following the conditions stated on the manufacturer's label and safety data sheet. Organosilicon and organohalogen building blocks of this type are best kept sealed to limit exposure to air and humidity. Handle in a fume hood using gloves, safety glasses and a laboratory coat, avoid inhalation of dust or vapour, and keep containers clearly labelled. Consult the safety data sheet before use and dispose of residues and contaminated materials through approved chemical waste channels.

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