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CAS 174508-31-7

2,5-Dibromo-3,4-ethylenedioxythiophene TCI D4056

2,5-Dibromo-3,4-ethylenedioxythiophene TCI D4056
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TCI D4056 2,5-Dibromo-3,4-ethylenedioxythiophene (CAS 174508-31-7) is the dibromo derivative of EDOT, the monomer that forms the backbone of the conductive polymer PEDOT. The compound belongs to the class of building blocks for polymer semiconductors, and its role in the laboratory is to supply an EDOT unit that has already been activated at both alpha positions of the thiophene ring. With those two bromine atoms in place, researchers can direct the formation of polymer chains or connect EDOT units to other units through transition-metal-catalysed coupling reactions, so the structure of the final material can be designed far more precisely than with ordinary oxidative polymerisation.

The distinguishing characteristic of this compound comes from the ethylenedioxy ring that caps positions 3 and 4. That group is a strong electron donor, so it lowers the oxidation potential of the material and yields polymers with a narrow band gap, high stability in the doped state, and clear electrochromic behaviour. Capping positions 3 and 4 also prevents irregular linkages from forming along the chain, so the resulting polymer is more ordered and its conductivity is more dependable. This combination is what makes EDOT derivatives a material of choice for electronic and electrochemical work.

In Indonesian laboratories, this building block is typically used in university and institutional research groups working on conductive polymers, organic electronics, and electrochemical sensing. It is normally handled at bench scale during monomer synthesis and coupling steps, then carried forward into polymerisation and device or electrode fabrication. Because it is supplied as a defined, ready-to-couple monomer, it fits well into research programmes that need reproducible starting material rather than in-house halogenation of EDOT.

  • Synthesis of PEDOT and PEDOT-based conductive polymers, where the two alpha-position bromines give controlled chain growth instead of the less predictable structure obtained from oxidative polymerisation.
  • Transition-metal-catalysed cross-coupling reactions, in which the dibromo functionality allows EDOT units to be joined to other aromatic or heteroaromatic units in a designed sequence.
  • Preparation of narrow band gap donor–acceptor copolymers, taking advantage of the strong electron-donating ethylenedioxy ring to lower the oxidation potential of the resulting material.
  • Development of electrochromic materials and devices, since EDOT-derived polymers show clear electrochromic behaviour together with high stability in their doped state.
  • Fabrication of organic electronic and electrochemical research materials, where the blocked 3 and 4 positions give regular chain linkages and therefore more reliable and reproducible conductivity.

Brand TCI
CAS number 174508-31-7
Molecular formula
Purity
Category Materials Science > Material Building Blocks > Polymer/Macromolecule Semiconductor Building Blocks
Pack sizes available in the standard research quantities listed for this TCI catalogue item
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Storage store according to the conditions stated on the manufacturer's label and safety data sheet
  • Chemical name: 2,5-Dibromo-3,4-ethylenedioxythiophene
  • Product code: D4056

Store the material in its original tightly closed container, in a cool, dry, well-ventilated place away from light, heat, ignition sources, and incompatible substances such as strong oxidising agents. Amber glass or the manufacturer's supplied packaging is suitable; keep the container sealed between uses to limit exposure to moisture and air, since brominated thiophene building blocks are normally handled as moisture-sensitive synthetic intermediates. Follow the storage temperature stated on the manufacturer's label and safety data sheet rather than assuming ambient conditions. Handle in a fume hood using safety glasses, chemical-resistant gloves, and a laboratory coat, avoid inhalation of dust and contact with skin and eyes, and dispose of residues and contaminated materials as chemical waste in line with institutional procedures. Consult the safety data sheet before first use.