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CS-W001157 4
Total: USD 88.00

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

  • CAS No. 480424-93-9

  • Cat. No. CS-W009452
  • Purity≥97%
  • MDL No.MFCD03789261

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

N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide|CS-W009452

Structure of 480424-93-9

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General Information

  • CAS No. 480424-93-9
  • Cat. No. CS-W009452
  • Purity ≥97%
  • MDL No. MFCD03789261
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₀BNO₃
  • Molecular Weight 261.12
  • Synonym(s) 3-Acetamidophenylboronic Acid Pinacol Ester
  • SMILES CC(NC1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1)=O

Description

N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide features a boronate ester group flanked by tetramethylcyclopentadienone rings, providing exceptional stability under standard conditions. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation with aryl halides. The acetamide moiety enhances solubility and facilitates downstream functionalization in synthetic workflows.

Application

N-(3-(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, making it ideal for constructing biaryl scaffolds in medicinal chemistry and materials science. Functional group tolerance supports integration into complex molecular architectures.

Synthesis

  • Route1

    References

    • WO2011/130628 A1, ; Page/Page column 169 ; WO 2011/130628 A1
  • Route2
    • N-(3-Chlorophenyl)acetamide|CS-0277313
      588-07-8
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~93%
    • In-stock
      N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide|CS-W009452
      480424-93-9

    References

    • Organic Letters, , vol. 13, # 21 p. 5766 - 5769
  • Route3
    • null|null
      108-24-7
    • In-stock
      3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-D1773
      210907-84-9
    • ~78%
    • In-stock
      N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide|CS-W009452
      480424-93-9

    References

    • US2008/269523 A1, ; Page/Page column 6 ;

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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