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Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate

  • CAS No. 957065-99-5

  • Cat. No. CS-0058615
  • Purity≥96%
  • MDL No.MFCD08063051

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

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate|CS-0058615

Structure of 957065-99-5

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General Information

  • CAS No. 957065-99-5
  • Cat. No. CS-0058615
  • Purity ≥96%
  • MDL No. MFCD08063051
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₈BNO₄
  • Molecular Weight 263.10
  • Synonym(s) 2-(Methoxycarbonyl)pyridine-5-boronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CN=C(C(OC)=O)C=C2)O1

Description

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate is a bench-stable boronate ester featuring a pyridine-linked methyl ester. This reagent integrates seamlessly into Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and solubility in organic solvents.

Application

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its stability under ambient conditions and compatibility with diverse functional groups enable reliable C–C bond formation in complex molecule synthesis. The picolinic ester moiety provides a handle for further derivatization, while the tetramethyl-substituted dioxaborolane enhances shelf life and reactivity in Suzuki-Miyaura couplings.

Synthesis

  • Route1

    References

    • WO2009/156966 A1, ; Page/Page column 38-39 ; WO 2009/156966 A1

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   57.65
  • LogP   1.1674
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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