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CS-W001157 4
Total: USD 88.00

4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

  • CAS No. 568577-88-8

  • Cat. No. CS-W014555
  • Purity≥96%
  • MDL No.MFCD04112544

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

4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine|CS-W014555

Structure of 568577-88-8

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General Information

  • CAS No. 568577-88-8
  • Cat. No. CS-W014555
  • Purity ≥96%
  • MDL No. MFCD04112544
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₄BNO₃
  • Molecular Weight 289.18
  • Synonym(s) 4-Morpholinophenylboronic Acid Pinacol Ester
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(N3CCOCC3)C=C2)O1

Description

4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine features a boronate ester handle flanked by a para-substituted phenyl ring and a morpholine heterocycle. This combination delivers enhanced solubility and stability under standard conditions, enabling efficient coupling in Suzuki-Miyaura reactions. The electron-rich morpholine moiety improves reactivity in cross-coupling processes while maintaining bench-stable handling characteristics.

Application

4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. The morpholine moiety provides solubility and functional group tolerance, while the stable tetramethylboronate group enables efficient coupling with aryl halides under mild conditions. This reagent facilitates rapid access to biaryl architectures common in medicinal chemistry and materials science, offering excellent bench stability and straightforward purification.

Synthesis

  • Route1
    • In-stock
      4-(4-Bromophenyl)morpholine|CS-W009360
      30483-75-1
    • null|null
      25015-63-8
    • ~84%
    • In-stock
      4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine|CS-W014555
      568577-88-8

    References

    • SMITHKLINE BEECHAM CORPORATION Patent: WO2004/13138 A2, 2004 ; Location in patent: Page 23; 24 ; WO 2004/013138 A2
  • Route2

    References

    • Yamamoto, Tetsuya; Morita, Tomoyuki; Takagi, Jun; Yamakawa, Tetsu Organic Letters, 2011 , vol. 13, # 21 p. 5766 - 5769
  • Route3

    References

    • Patel, Gautam; Karver, Caitlin E.; Behera, Ranjan; Guyett, Paul J.; Sullenberger, Catherine; Edwards, Peter; Roncal, Norma E.; Mensa-Wilmot, Kojo; Pollastri, Michael P. Journal of Medicinal Chemistry, 2013 , vol. 56, # 10 p. 3820 - 3832

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

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Computational Chemistry Data

  • TPSA   30.93
  • LogP   1.8224
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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