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CS-W001157 4
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4,4,5,5-Tetramethyl-2-(3-thienyl)-1,3,2-dioxaborolane

  • CAS No. 214360-70-0

  • Cat. No. CS-0043239
  • Purity≥95%
  • MDL No.MFCD05663893

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

4,4,5,5-Tetramethyl-2-(3-thienyl)-1,3,2-dioxaborolane|CS-0043239

Structure of 214360-70-0

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General Information

  • CAS No. 214360-70-0
  • Cat. No. CS-0043239
  • Purity ≥95%
  • MDL No. MFCD05663893
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₅BO₂S
  • Molecular Weight None
  • Synonym(s) Thiophene-3-boronic acid, pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CSC=C2)O1

Description

This boronate ester features a thienyl group at the 2-position, enhancing electron density and enabling efficient cross-coupling in Suzuki-Miyaura reactions. The tetramethyl-substituted dioxaborolane ring imparts exceptional stability under ambient conditions, while maintaining high reactivity when activated. Ideal for constructing complex heteroaromatic architectures with minimal decomposition.

Application

4,4,5,5-Tetramethyl-2-(3-thienyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The thienyl group enables efficient incorporation into heteroaromatic scaffolds common in pharmaceuticals and materials science. Its tetramethyl substitution enhances reagent stability and simplifies purification, while the dioxaborolane ring facilitates reliable coupling under mild conditions.

Synthesis

  • Route1

    References

    • Billingsley, Kelvin L.; Barder, Timothy E.; Buchwald, Stephen L. Angewandte Chemie - International Edition, 2007 , vol. 46, # 28 p. 5359 - 5363
  • Route2
    • In-stock
      3-Bromothiophene|CS-W009226
      872-31-1
    • null|null
      25015-63-8
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(3-thienyl)-1,3,2-dioxaborolane|CS-0043239
      214360-70-0

    References

    • US6680401 B1, ; Page column 59 ;
  • Route3

    References

    • Asachenko, Andrey F.; Sorochkina, Kristina R.; Dzhevakov, Pavel B.; Topchiy, Maxim A.; Nechaev, Mikhail S. Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3553 - 3557

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   18.46
  • LogP   2.0473
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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