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1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

  • CAS No. 1160790-84-0

  • Cat. No. CS-0041736
  • Purity≥95%
  • MDL No.MFCD12032569

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

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one|CS-0041736

Structure of 1160790-84-0

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General Information

  • CAS No. 1160790-84-0
  • Cat. No. CS-0041736
  • Purity ≥95%
  • MDL No. MFCD12032569
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₈BNO₃
  • Molecular Weight 235.09
  • Synonym(s) 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one
  • SMILES O=C1C=C(B2OC(C)(C)C(C)(C)O2)C=CN1C

Description

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one features a boronate ester group integrated into a pyridinone scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent facilitates rapid construction of biaryl architectures in late-stage functionalization and medicinal chemistry workflows.

Application

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one serves as a versatile boronate building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its pyridinone core provides enhanced stability and solubility, while the tetramethylboronate moiety ensures high reactivity and functional group tolerance. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis of biologically active heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • PROLYSIS LTD Patent: WO2009/74812 A1, 2009 ; Location in patent: Page/Page column 73 ; WO 2009/074812 A1
  • Route2

    References

    • INCYTE CORPORATION; ZHANG, Colin; QIAN, Ding-quan; ZHUO, Jincong; YAO, Wenqing Patent: WO2010/75270 A1, 2010 ; Location in patent: Page/Page column 89-90 ; WO 2010/075270 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   40.46
  • LogP   0.6845
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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