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CS-W001157 4
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1-Methylpyrrole-2-boronic acid pinacol ester

  • CAS No. 850567-47-4

  • Cat. No. CS-0006834
  • Purity≥97%
  • MDL No.MFCD06659917

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

1-Methylpyrrole-2-boronic acid pinacol ester|CS-0006834

Structure of 850567-47-4

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General Information

  • CAS No. 850567-47-4
  • Cat. No. CS-0006834
  • Purity ≥97%
  • MDL No. MFCD06659917
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₈BNO₂
  • Molecular Weight 207.08
  • Synonym(s) 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole
  • SMILES CC1(C)C(C)(C)OB(C2=CC=CN2C)O1

Description

1-Methylpyrrole-2-boronic acid pinacol ester offers a bench-stable, moisture-tolerant boronate handle for Suzuki-Miyaura couplings. The electron-rich pyrrole moiety enhances reactivity in palladium-catalyzed transformations, while the pinacol protection ensures ease of handling and storage under standard conditions.

Application

1-Methylpyrrole-2-boronic acid pinacol ester serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its pyrrolic framework enables efficient integration into heterocyclic scaffolds common in medicinal chemistry, with the pinacol ester enhancing solubility and minimizing protodeboronation. The methyl group provides electronic tuning and improves functional group tolerance in complex molecule synthesis.

Synthesis

  • Route1

    References

    • THE UNIVERSITY OF MANCHESTER; INGLESON, Michael James Patent: WO2012/25760 A1, 2012 ; Location in patent: Page/Page column 56-57 ;
  • Route2

    References

    • Angewandte Chemie - International Edition, , vol. 50, # 9 p. 2102 - 2106
  • Route3
    • null|null
      96-54-8
    • null|null
      25015-63-8
    • ~3%
    • In-stock
      1-Methylpyrrole-2-boronic acid pinacol ester|CS-0006834
      850567-47-4

    References

    • Mertins, Kristin; Zapf, Alexander; Beller, Matthias Journal of Molecular Catalysis A: Chemical, 2004 , vol. 207, # 1 p. 21 - 25

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

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Computational Chemistry Data

  • TPSA   23.39
  • LogP   1.3243
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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