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CS-W001157 4
Total: USD 88.00

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

  • CAS No. 364794-80-9

  • Cat. No. CS-0045008
  • Purity≥97%
  • MDL No.MFCD06797489

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

4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine|CS-0045008

Structure of 364794-80-9

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General Information

  • CAS No. 364794-80-9
  • Cat. No. CS-0045008
  • Purity ≥97%
  • MDL No. MFCD06797489
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₆BNO₃
  • Molecular Weight 303.20
  • Synonym(s) 3-(4-Morpholinylmethyl)benzeneboronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CC(CN3CCOCC3)=CC=C2)O1

Application

4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The morpholine moiety provides solubility and metabolic stability, while the pinacol borane group enables reliable coupling under mild conditions. This compound exhibits excellent bench stability, facilitates purification by standard chromatography, and functions effectively in late-stage functionalization of bioactive scaffolds.

Synthesis

  • Route1
    • null|null
      110-91-8
    • In-stock
      (3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol|CS-W000934
      443776-76-9
    • ~79%
    • In-stock
      4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine|CS-0045008
      364794-80-9

    References

    • Ma, Winson M. J.; James, Tony D.; Williams, Jonathan M. J. Organic Letters, 2013 , vol. 15, # 18 p. 4850 - 4853
  • Route2
    • null|null
      110-91-8
    • In-stock
      2-(3-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W009968
      214360-74-4
    • ~96%
    • In-stock
      4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine|CS-0045008
      364794-80-9

    References

    • Spencer, John; Baltus, Christine B.; Patel, Hiren; Press, Neil J.; Callear, Samantha K.; Male, Louise; Coles, Simon J. ACS Combinatorial Science, 2011 , vol. 13, # 1 p. 24 - 31
  • Route3
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • 4-(3-Bromobenzyl)morpholine|CS-0197188
      364793-82-8
    • ~%
    • In-stock
      4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine|CS-0045008
      364794-80-9

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 12, # 20 p. 2989 - 2992

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   30.93
  • LogP   1.818
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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