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CS-W001157 4
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Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

  • CAS No. 1025718-91-5

  • Cat. No. CS-W004025
  • Purity≥97%
  • MDL No.MFCD09027079

*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)nicotinate|CS-W004025

Structure of 1025718-91-5

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General Information

  • CAS No. 1025718-91-5
  • Cat. No. CS-W004025
  • Purity ≥97%
  • MDL No. MFCD09027079
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₈BNO₄
  • Molecular Weight 263.10
  • Synonym(s) 3-(Methoxycarbonyl)Pyridine-5-Boronic Acid, Pinacol Ester
  • SMILES COC(=O)c1cncc(c1)B1OC(C(O1)(C)C)(C)C

Description

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate 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 common organic solvents.

Application

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety enables efficient coupling with aryl and vinyl halides under mild conditions, while the methyl nicotinate group provides a versatile handle for downstream functionalization. Its high stability, excellent functional group tolerance, and ease of purification make it a practical choice for constructing biaryl and heteroaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Angewandte Chemie - International Edition, , vol. 51, # 2 p. 540 - 543
  • Route2

    References

    • XCOVERY, INC. Patent: WO2008/88881 A1, 2008 ; Location in patent: Page/Page column 49 ; WO 2008/088881 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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