• 3,4-Dibromothieno[2,3-b]thiophene (CAS 53255-78-0) - TCI D4033 - AMI Scientific
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TCI

CAS 53255-78-0

3,4-Dibromothieno[2,3-b]thiophene TCI D4033

3,4-Dibromothieno[2,3-b]thiophene TCI D4033
Rp 12.189.450,00
Rp 12.189.450,00
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TCI D4033 3,4-Dibromothieno[2,3-b]thiophene is a semiconductor building block based on a thieno[2,3-b]thiophene core in which two bromine atoms occupy positions 3 and 4, the lateral positions of the fused ring framework. This substitution pattern distinguishes it fundamentally from the 2,5-dibromo isomer, because the connection points do not lie along the long axis of the molecule but rather on the side of the ring system. In materials science and synthetic chemistry laboratories, this compound is used when researchers wish to install substituents at the lateral positions of the thienothiophene skeleton — for example, to build branches, to add solubilizing chains, or to construct molecular architectures that are not linear.

The characteristic that makes this isomer the preferred choice is the molecular design flexibility it offers. With bromine at positions 3 and 4, positions 2 and 5 remain free and can be functionalized afterwards through directed lithiation or subsequent coupling reactions. This allows a stepwise synthesis toward fully substituted molecules following a controlled pattern. The two neighbouring bromine atoms also open the possibility of annulation reactions to form additional rings fused at the lateral side, a strategy commonly used to extend the conjugated framework. Chemists therefore treat this reagent as a versatile branch point rather than a simple linear linker.

In Indonesian laboratories, this material building block is typically handled in university and institutional research groups working on organic electronics, conjugated polymers, and molecular semiconductors. It is generally used at small synthetic scale on the bench, within schemes where the thienothiophene core is elaborated step by step before being carried forward into coupling or polymerization work. Because it is supplied as a catalogue research chemical, it is normally ordered per experiment and stored under controlled laboratory conditions between synthetic campaigns.

  • Cross-coupling chemistry: the two bromine atoms at positions 3 and 4 serve as reactive handles for palladium-catalysed coupling, allowing substituents to be attached at the lateral sides of the fused core.
  • Non-linear molecular architecture: because the connection points are not on the long molecular axis, the compound suits construction of branched or angled frameworks rather than strictly linear backbones.
  • Stepwise selective functionalization: with positions 2 and 5 left free, chemists can carry out directed lithiation or later coupling to reach fully substituted molecules under a controlled sequence.
  • Annulation and ring extension: the adjacent bromine pair supports annulation reactions that fuse additional rings onto the lateral side, a common strategy for extending the conjugated framework.
  • Solubilizing chain attachment: the lateral positions provide convenient points for installing side chains that improve processability of thienothiophene-based semiconductor materials.

Brand TCI (Tokyo Chemical Industry)
CAS number 53255-78-0
Molecular formula —
Purity —
Category Materials Science > Material Building Blocks > Polymer/Macromolecule Semiconductor Building Blocks
Pack sizes as listed in the current TCI catalogue entry for this item
Physical form —
Storage —
  • Catalogue number: D4033
  • Chemical name: 3,4-Dibromothieno[2,3-b]thiophene

Store this reagent in its original tightly closed container, protected from light, moisture, and heat, and follow the storage temperature stated on the manufacturer's label and safety data sheet. Amber glass or the supplier's original packaging is suitable; keep the container in a dedicated chemical cabinet away from oxidizing agents and ignition sources. Handle only in a well-ventilated fume hood, wearing safety goggles, a laboratory coat, and chemically resistant gloves. Avoid inhalation of dust and contact with skin or eyes. Weigh and transfer using clean, dry glassware and spatulas to prevent contamination and moisture uptake, and reseal promptly after use. Dispose of residues and contaminated consumables as halogenated organic chemical waste in accordance with institutional procedures. Review the current safety data sheet before first use.

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