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CS-W001157 4
Total: USD 88.00

[2,2'-Bithiophen]-5-ylboronic acid

  • CAS No. 132898-95-4

  • Cat. No. CS-0173966
  • Purity≥98%
  • MDL No.None

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

[2,2'-Bithiophen]-5-ylboronic acid|CS-0173966

Structure of 132898-95-4

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General Information

  • CAS No. 132898-95-4
  • Cat. No. CS-0173966
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BO₂S₂
  • Molecular Weight 210.08
  • Synonym(s) 2,2-Bithiophene-5-Boronic Acid
  • SMILES OB(O)C(S1)=CC=C1C2=CC=CS2

Description

This boronate moiety integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, delivering high yields under standard conditions. The bithiophene scaffold imparts enhanced stability and solubility, enabling efficient functionalization of conjugated systems in organic electronics and materials science applications.

Application

[2,2'-Bithiophen]-5-ylboronic acid serves as a versatile building block in cross-coupling chemistry, enabling efficient Suzuki-Miyaura reactions to construct biaryl motifs. Its stability under ambient conditions and compatibility with diverse functional groups make it well-suited for the synthesis of conjugated materials and heterocyclic scaffolds relevant to organic electronics and medicinal chemistry.

Synthesis

  • Route1

    References

    • Kim, Dae-Sik; Kyo, Han Ahn Journal of Organic Chemistry, 2008 , vol. 73, # 17 p. 6831 - 6834
  • Route2
    • null|null
      121-43-7
    • In-stock
      2-(2-Thienyl)thiophen|CS-W008787
      492-97-7
    • ~71%
    • null|null
      651329-37-2
    • In-stock
      [2,2'-Bithiophen]-5-ylboronic acid|CS-0173966
      132898-95-4

    References

    • Toyo Gosei Co., Ltd. Patent: EP1535942 A1, 2005 ;
  • Route3
    • null|null
      3480-11-3
    • ~98%
    • In-stock
      [2,2'-Bithiophen]-5-ylboronic acid|CS-0173966
      132898-95-4

    References

    • Katagiri, Toshifumi; Ota, Satoshi; Ohira, Takayuki; Yamao, Takeshi; Hotta, Shu Journal of Heterocyclic Chemistry, 2007 , vol. 44, # 4 p. 853 - 862

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   40.46
  • LogP   1.1564
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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