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CS-W001157 4
Total: USD 88.00

2,4-Dibromothiophene

  • CAS No. 3140-92-9

  • Cat. No. CS-M0432
  • Purity≥93%
  • MDL No.MFCD00043889

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

2,4-Dibromothiophene|CS-M0432

Structure of 3140-92-9

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General Information

  • CAS No. 3140-92-9
  • Cat. No. CS-M0432
  • Purity ≥93%
  • MDL No. MFCD00043889
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₂Br₂S
  • Molecular Weight 241.93
  • Synonym(s) 2,3-THIOEPOXY MADOL
  • SMILES BrC1=CSC(Br)=C1

Description

2,4-Dibromothiophene is a brominated heterocyclic compound featuring two bromine substituents at the 2- and 4-positions of the thiophene ring. This configuration imparts enhanced electrophilic reactivity and facilitates palladium-catalyzed cross-coupling reactions in synthetic organic chemistry. The molecule exhibits good stability under standard bench conditions and serves as a key intermediate in the construction of functionalized aromatic systems for materials science and pharmaceutical applications.

Application

2,4-Dibromothiophene serves as a versatile building block in the synthesis of functionalized heterocycles and conjugated materials. The bromine substituents enable efficient palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, with high regioselectivity. Its bench-stable nature and compatibility with diverse reaction conditions make it ideal for constructing complex molecular architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 2,3,5-Tribromothiophene|CS-W012003
      3141-24-0
    • ~89%
    • In-stock
      2,4-Dibromothiophene|CS-M0432
      3140-92-9

    References

    • Journal of Chemical Research - Part S, , # 3 p. 150 - 151
  • Route2
    • null|null
      3141-27-3
    • ~95%
    • In-stock
      2,4-Dibromothiophene|CS-M0432
      3140-92-9

    References

    • Heterocycles, , vol. 20, # 10 p. 2035 - 2037
  • Route3
    • 2,3,5-Tribromothiophene|CS-W012003
      3141-24-0
    • null|null
      5713-61-1
    • ~17%
    • In-stock
      2,4-Dibromothiophene|CS-M0432
      3140-92-9
    • 4,5-Dibromo-2,2'-bithiophene|CS-0683504
      1006384-44-6
    • In-stock
      2-(2-Thienyl)thiophen|CS-W008787
      492-97-7
    • 3'-Bromo-2,2':5',2''-terthiophene|CS-0168065
      105125-00-6

    References

    • European Journal of Organic Chemistry, , # 5 p. 801 - 804

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06
Signal Word : Danger
UN#: 2810
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.2731
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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