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CS-W001157 4
Total: USD 88.00

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

  • CAS No. 214360-60-8

  • Cat. No. CS-0097879
  • Purity≥97%
  • MDL No.MFCD02093722

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

N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide|CS-0097879

Structure of 214360-60-8

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General Information

  • CAS No. 214360-60-8
  • Cat. No. CS-0097879
  • Purity ≥97%
  • MDL No. MFCD02093722
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₀BNO₃
  • Molecular Weight 261.12
  • Synonym(s) N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide
  • SMILES CC(NC1=CC=C(C=C1)B2OC(C)(C(C)(O2)C)C)=O

Description

N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide features a boronate ester group enabling robust Suzuki-Miyaura coupling under mild conditions. The acetamide moiety enhances solubility and stability, while the tetramethyl-substituted dioxaborolane resists protodeboronation. This compound integrates efficiently into complex molecular architectures with high functional group tolerance.

Application

N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pinacol boronate group enables stable, bench-ready handling and orthogonal reactivity under mild conditions. It facilitates efficient C–C bond formation with aryl halides and triflates, supporting the construction of biaryl scaffolds commonly found in pharmaceutical intermediates and functional materials.

Synthesis

  • Route1
    • In-stock
      N-(4-Iodophenyl)acetamide|CS-W004143
      622-50-4
    • null|null
      25015-63-8
    • ~78%
    • In-stock
      N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide|CS-0097879
      214360-60-8

    References

    • US6680401 B1, ; Page column 19 ;
  • Route2
    • null|null
      75-36-5
    • In-stock
      4-Aminophenylboronic acid pinacol ester|CS-M0336
      214360-73-3
    • ~91%
    • In-stock
      N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide|CS-0097879
      214360-60-8

    References

    • WO2006/51851 A1, ; Page/Page column 73 ;
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 65, # 1 p. 164 - 168

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   47.56
  • LogP   1.9442
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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