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CS-W001157 4
Total: USD 88.00

3,6-Dibromothieno[3,2-b]thiophene

  • CAS No. 392662-65-6

  • Cat. No. CS-W008431
  • Purity≥98%
  • MDL No.MFCD10000958

*For research and further manufacturing use only, not for direct human use.

3,6-Dibromothieno[3,2-b]thiophene|CS-W008431

Structure of 392662-65-6

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General Information

  • CAS No. 392662-65-6
  • Cat. No. CS-W008431
  • Purity ≥98%
  • MDL No. MFCD10000958
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₂Br₂S₂
  • Molecular Weight 298.02
  • Synonym(s) thieno[3,2-b]thiophene, 3,6-dibromo-
  • SMILES BrC1=CSC2=C1SC=C2Br

Description

3,6-Dibromothieno[3,2-b]thiophene is a brominated heterocyclic scaffold featuring two electrophilic bromine substituents at the 3 and 6 positions. This configuration enables efficient cross-coupling reactions in materials synthesis, particularly for constructing conjugated polymers and small-molecule semiconductors. The molecule exhibits enhanced solubility and processability compared to its non-halogenated analogs.

Application

3,6-Dibromothieno[3,2-b]thiophene serves as a versatile building block for the synthesis of functionalized thiophene-based materials. Its dibromo substitution pattern enables efficient palladium-catalyzed cross-coupling reactions, facilitating the construction of conjugated polymers and small-molecule semiconductors. The compound exhibits good bench stability and compatibility with standard reaction conditions, making it well-suited for iterative synthetic workflows in organic electronics and materials chemistry.

Synthesis

  • Route1
    • null|null
      25121-87-3
    • ~99%
    • In-stock
      3,6-Dibromothieno[3,2-b]thiophene|CS-W008431
      392662-65-6

    References

    • Biniek, Laure; Schroeder, Bob C.; Donaghey, Jenny E.; Yaacobi-Gross, Nir; Ashraf, Raja Shahid; Soon, Ying W.; Nielsen, Christian B.; Durrant, James R.; Anthopoulos, Thomas D.; McCulloch, Iain Macromolecules, 2013 , vol. 46, # 3 p. 727 - 735
  • Route2

    References

    • Fuller, Lance S.; Iddon, Brian; Smith, Kevin A. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 22 p. 3465 - 3470
  • Route3

    References

    • Biniek, Laure; Schroeder, Bob C.; Donaghey, Jenny E.; Yaacobi-Gross, Nir; Ashraf, Raja Shahid; Soon, Ying W.; Nielsen, Christian B.; Durrant, James R.; Anthopoulos, Thomas D.; McCulloch, Iain Macromolecules, 2013 , vol. 46, # 3 p. 727 - 735

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   4.4878
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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