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NSC 109395

  • CAS No. 7311-70-8

  • Cat. No. CS-0030487
  • Purity≥97%
  • MDL No.MFCD08445656

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

NSC 109395|CS-0030487

Structure of 7311-70-8

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General Information

  • CAS No. 7311-70-8
  • Cat. No. CS-0030487
  • Purity ≥97%
  • MDL No. MFCD08445656
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₂Br₂O₂S
  • Molecular Weight 285.94
  • Synonym(s) 2,5-Dibromothiophene-3-carboxylic acid
  • SMILES O=C(C1=C(Br)SC(Br)=C1)O

Description

2,5-Dibromothiophene-3-carboxylic acid features a rigid thiophene core bearing bromine substituents at the 2 and 5 positions and a carboxylic acid group at the 3 position. This arrangement enables direct functionalization in cross-coupling reactions, offering high reactivity under palladium catalysis. The molecule exhibits excellent stability under standard conditions, facilitating straightforward integration into complex molecular architectures for materials science and pharmaceutical applications.

Application

2,5-Dibromothiophene-3-carboxylic acid serves as a versatile building block for the synthesis of functionalized thiophene-based scaffolds in medicinal chemistry and materials science. The carboxylic acid group enables direct derivatization via amide coupling or esterification, while the dibromo substitution pattern facilitates palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Stille couplings. Its bench-stable crystalline form and orthogonal reactivity support efficient multistep synthesis with high functional group tolerance.

Synthesis

  • Route1

    References

    • Kim, Dae-Sik; Kyo, Han Ahn Journal of Organic Chemistry, 2008 , vol. 73, # 17 p. 6831 - 6834
  • Route2

    References

    • VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2005/103050 A2, 2005 ; Location in patent: Page/Page column 187 ; WO 2005/103050 A2
  • Route3
    • 2,5-Dibromothiophene-3-carbaldehyde|CS-0075696
      1193-69-7
    • ~%
    • In-stock
      NSC 109395|CS-0030487
      7311-70-8

    References

    • Fournari,P. et al. Bulletin de la Societe Chimique de France, 1967 , p. 4115 - 4120

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   37.3
  • LogP   2.9713
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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