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

  • CAS No. 885692-91-1

  • Cat. No. CS-0051125
  • Purity≥95%
  • MDL No.None

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

4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0051125

Structure of 885692-91-1

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General Information

  • CAS No. 885692-91-1
  • Cat. No. CS-0051125
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇BO₂S
  • Molecular Weight 224.13
  • Synonym(s) 3-Methyl-2-thiopheneboronic Acid Pinacol Ester
  • SMILES CC1=C(SC=C1)B1OC(C)(C)C(C)(C)O1

Description

This boronate moiety integrates a 3-methylthiophene unit with a tetramethyl-substituted dioxaborolane ring, delivering enhanced stability and compatibility in Suzuki-Miyaura cross-coupling reactions. The sterically protected boron center facilitates efficient coupling under mild conditions, while the electron-rich thiophene group enables selective functionalization in complex molecular architectures.

Application

4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane core enhances air and moisture stability while maintaining high reactivity under standard catalytic conditions. It facilitates efficient coupling with aryl halides and pseudohalides, enabling rapid construction of biaryl and heteroaryl scaffolds commonly found in pharmaceutical intermediates and functional materials.

Synthesis

  • Route1
    • null|null
      61676-62-8
    • ~54%
    • In-stock
      4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0051125
      885692-91-1

    References

    • Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; Meegalla, Sanath K.; Rudolph, M. Jonathan; Wall, Mark J.; Wilson, Kenneth J.; Desjarlais, Renee L.; Manthey, Carl L.; Molloy, Christopher J. Patent: US2008/51402 A1, 2008 ; Location in patent: Page/Page column 35 ; US 20080051402 A1
  • Route2
    • In-stock
      2-Bromo-3-methylthiophene|CS-W002276
      14282-76-9
    • null|null
      61676-62-8
    • ~52%
    • In-stock
      4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0051125
      885692-91-1

    References

    • JANSSEN PHARMACEUTICA N.V. Patent: WO2007/48088 A2, 2007 ; Location in patent: Page/Page column 61-62 ; WO 2007/048088 A2
  • Route3
    • null|null
      616-44-4
    • null|null
      25015-63-8
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0051125
      885692-91-1
    • In-stock
      4,4,5,5-Tetramethyl-2-(4-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0091600
      635305-48-5

    References

    • Tetrahedron, , vol. 64, # 26 p. 6103 - 6114

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   2.35572
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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