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CS-W001157 4
Total: USD 88.00

2-(3,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 754226-39-6

  • Cat. No. CS-0176974
  • Purity≥98%
  • MDL No.None

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

2-(3,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0176974

Structure of 754226-39-6

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General Information

  • CAS No. 754226-39-6
  • Cat. No. CS-0176974
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅BF₂O₂
  • Molecular Weight 240.05
  • Synonym(s) None
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(F)C(F)=C2)O1

Description

This boronate ester features a 3,4-difluorophenyl group linked to a tetramethyl-1,3,2-dioxaborolane scaffold, delivering enhanced stability and reactivity in Suzuki-Miyaura cross-coupling reactions. The electron-withdrawing fluorine substituents modulate electronic properties for improved coupling efficiency, while the steric bulk of the tetramethyl groups ensures bench-stable handling and resistance to hydrolysis under standard conditions.

Application

2-(3,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its tetramethyl-substituted dioxaborolane ring enhances air and moisture stability while maintaining high reactivity with aryl halides and triflates. The 3,4-difluorophenyl moiety offers orthogonal functional group compatibility and enables efficient construction of biaryl scaffolds prevalent in pharmaceutical and agrochemical research.

Synthesis

  • Route1
    • null|null
      348-61-8
    • null|null
      25015-63-8
    • ~95%
    • In-stock
      2-(3,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0176974
      754226-39-6

    References

    • Pintaric, Christine; Olivero, Sandra; Gimbert, Yves; Chavant, Pierre Y.; Dunach, Elisabet Journal of the American Chemical Society, 2010 , vol. 132, # 34 p. 11825 - 11827
  • Route2
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • 3,4-Difluoroaniline Gefitinib Impurity|CS-0167147
      3863-11-4
    • ~65%
    • In-stock
      2-(3,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0176974
      754226-39-6

    References

    • Qiu, Di; Jin, Liang; Zheng, Zhitong; Meng, He; Mo, Fanyang; Wang, Xi; Zhang, Yan; Wang, Jianbo Journal of Organic Chemistry, 2013 , vol. 78, # 5 p. 1923 - 1933
  • Route3
    • null|null
      348-61-8
    • ~%
    • In-stock
      2-(3,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0176974
      754226-39-6

    References

    • Takagi, Jun; Yamakawa, Tetsu Tetrahedron Letters, 2013 , vol. 54, # 2 p. 166 - 169

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.264
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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