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

  • CAS No. 1218791-25-3

  • Cat. No. CS-0175482
  • Molecule weight262.11
  • Purity≥97%
  • MDL No.MFCD11878275

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

N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinamide|CS-0175482

Structure of 1218791-25-3

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General Information

  • CAS No. 1218791-25-3
  • Cat. No. CS-0175482
  • Purity ≥97%
  • MDL No. MFCD11878275
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BN₂O₃
  • Molecular Weight 262.11
  • Synonym(s) N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-Pyridinecarboxamide
  • SMILES CC1(C)C(OB(C2=CN=CC(C(NC)=O)=C2)O1)(C)C

Description

N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinamide delivers a boronate ester group coupled to a methylated nicotinamide core, enabling efficient Suzuki-Miyaura coupling under standard conditions. This bench-stable reagent integrates readily into complex molecule synthesis, offering enhanced solubility and compatibility with diverse reaction systems.

Application

N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinamide serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient palladium-catalyzed coupling with aryl and heteroaryl halides under mild conditions. Its stability in air and moisture facilitates handling, while the N-methylpyridine scaffold provides orthogonal reactivity for downstream functionalization. This compound is particularly valuable in constructing bioactive heterocyclic frameworks and pharmaceutical intermediates.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   60.45
  • LogP   0.7404
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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