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CS-W001157 4
Total: USD 88.00

2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene

  • CAS No. 175361-81-6

  • Cat. No. CS-0091655
  • Purity≥97%
  • MDL No.MFCD09800563

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

2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene|CS-0091655

Structure of 175361-81-6

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General Information

  • CAS No. 175361-81-6
  • Cat. No. CS-0091655
  • Purity ≥97%
  • MDL No. MFCD09800563
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₆B₂O₄S
  • Molecular Weight 336.06
  • Synonym(s) Thiophene-2,5-diboronic Acid Bis(pinacol) Ester
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(B3OC(C)(C)C(C)(C)O3)S2)O1

Description

This boronate-functionalized thiophene integrates readily into Suzuki-Miyaura coupling reactions under standard conditions, delivering conjugated architectures with high fidelity. The tetramethyl-substituted dioxaborolane moieties confer exceptional stability and moisture tolerance, enabling reliable handling and reproducible cross-coupling outcomes in synthetic workflows.

Application

2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene serves as a versatile Suzuki coupling partner, enabling efficient construction of biaryl and heteroaryl architectures. The diborane moiety offers excellent stability under ambient conditions, facilitates mild reaction termination, and supports orthogonal functional group tolerance in complex molecule assembly. Its predictable reactivity and ease of purification make it a reliable building block for pharmaceutical and materials science applications.

Synthesis

  • Route1
    • null|null
      188290-36-0
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~78%
    • In-stock
      2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene|CS-0091655
      175361-81-6

    References

    • Takagi, Jun; Sato, Kazuaki; Hartwig, John F; Ishiyama, Tatsuo; Miyaura, Norio Tetrahedron Letters, 2002 , vol. 43, # 32 p. 5649 - 5651
  • Route2
    • null|null
      188290-36-0
    • null|null
      61676-62-8
    • ~51%
    • In-stock
      2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene|CS-0091655
      175361-81-6

    References

    • Usta, Hakan; Lu, Gang; Facchetti, Antonio; Marks, Tobin J. Journal of the American Chemical Society, 2006 , vol. 128, # 28 p. 9034 - 9035
  • Route3
    • null|null
      3141-27-3
    • null|null
      61676-62-8
    • ~93%
    • In-stock
      2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene|CS-0091655
      175361-81-6

    References

    • Capan, Asli; Veisi, Hojat; Goren, Ahmet C.; Ozturk, Turan Macromolecules, 2012 , vol. 45, # 20 p. 8228 - 8236

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

Quality Control

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Computational Chemistry Data

  • TPSA   36.92
  • LogP   2.3465
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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