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5-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

  • CAS No. 445264-60-8

  • Cat. No. CS-D1055
  • Molecule weight235.09
  • Purity≥98%
  • MDL No.MFCD03412068

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

5-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-D1055

Structure of 445264-60-8

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General Information

  • CAS No. 445264-60-8
  • Cat. No. CS-D1055
  • Purity ≥98%
  • MDL No. MFCD03412068
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₈BNO₃
  • Molecular Weight 235.09
  • Synonym(s) Pyridine, 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
  • SMILES COC1=CN=CC(B2OC(C)(C)C(C)(C)O2)=C1

Description

5-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling under mild conditions. The electron-rich pyridine core enhances reactivity, while the tetramethyl-substituted dioxaborolane imparts stability and moisture tolerance. This compound integrates readily into complex molecular architectures during late-stage functionalization.

Application

5-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables robust coupling under mild conditions, while the pyridine core provides a stable heterocyclic scaffold with enhanced solubility and functional group tolerance. Bench-stable and readily purified by flash chromatography, it facilitates efficient construction of biaryl and heteroaryl architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • WO2009/74812 A1, ; Page/Page column 68 ; WO 2009/074812 A1
  • Route2

    References

    • Chemical Communications, , vol. 47, # 30 p. 8605 - 8607
  • Route3

    References

    • Chemical Communications, , vol. 47, # 30 p. 8605 - 8607

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   40.58
  • LogP   1.3894
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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