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CS-W001157 4
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5-Bromo-2,2'-bithiophene-5'-carboxaldehyde

  • CAS No. 110046-60-1

  • Cat. No. CS-0168061
  • Purity≥95%
  • MDL No.MFCD01321134

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

5-Bromo-2,2'-bithiophene-5'-carboxaldehyde|CS-0168061

Structure of 110046-60-1

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General Information

  • CAS No. 110046-60-1
  • Cat. No. CS-0168061
  • Purity ≥95%
  • MDL No. MFCD01321134
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅BrOS₂
  • Molecular Weight None
  • Synonym(s) 5-Bromo-5'-formyl-2,2'-bithiophene
  • SMILES O=CC1=CC=C(C2=CC=C(Br)S2)S1

Description

5-Bromo-2,2'-bithiophene-5'-carboxaldehyde features a brominated bithiophene core with a terminal aldehyde group, enabling direct coupling in cross-coupling reactions. The electron-deficient aldehyde facilitates conjugation and functionalization, while the bromine atom serves as a handle for palladium-catalyzed transformations. This compound integrates readily into π-conjugated systems for organic electronics and synthetic intermediates.

Application

5-Bromo-2,2'-bithiophene-5'-carboxaldehyde serves as a versatile building block for conjugated materials and heterocyclic synthesis. The aldehyde functionality enables direct coupling in Ullmann-type reactions and Suzuki-Miyaura protocols, while the bromo group offers orthogonal reactivity for palladium-catalyzed cross-couplings. Its bench-stable nature and compatibility with standard purification methods make it well-suited for iterative synthetic sequences in organic electronics and medicinal chemistry applications.

Synthesis

  • Route1

    References

    • Herbivo, Cyril; Comel, Alain; Kirsch; Raposo, M. Manuela M. Tetrahedron, 2009 , vol. 65, # 10 p. 2079 - 2086
  • Route2
    • In-stock
      5,5'-Dibromo-2,2'-bithiophene|CS-W013945
      4805-22-5
    • null|null
      68-12-2
    • ~65%
    • In-stock
      5-Bromo-2,2'-bithiophene-5'-carboxaldehyde|CS-0168061
      110046-60-1

    References

    • Kuo, Cheng-Yu; Huang, Yu-Chen; Hsiow, Chuen-Yo; Yang, Yu-Wen; Huang, Ching-I; Rwei, Syang-Peng; Wang, Hsing-Lin; Wang, Leeyih Macromolecules, 2013 , vol. 46, # 15 p. 5985 - 5997
  • Route3

    References

    • Chemistry - A European Journal, , vol. 11, # 16 p. 4735 - 4742

Safety Information

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GHS Pictogram : N/A
GHS No : N/A
Signal Word : N/A
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   4.0516
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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