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N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide

  • CAS No. 1006876-27-2

  • Cat. No. CS-0153831
  • Purity≥97%
  • MDL No.MFCD08458484

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

N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide|CS-0153831

Structure of 1006876-27-2

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General Information

  • CAS No. 1006876-27-2
  • Cat. No. CS-0153831
  • Purity ≥97%
  • MDL No. MFCD08458484
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₁BN₂O₃
  • Molecular Weight 276.14
  • Synonym(s) N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide
  • SMILES CC1(C)C(C)(C)OB(C2=CN=C(C=C2)C(=O)N(C)C)O1

Description

N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide features a boronate ester group paired with a pyridine amide motif, enabling efficient cross-coupling under mild conditions. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura reactions, offering predictable regiochemistry and compatibility with diverse functional groups.

Application

N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide serves as a versatile boron-containing building block for palladium-catalyzed cross-coupling reactions. The picolinamide moiety provides a robust nitrogen-directed coupling site, while the pinacol boronate ester ensures excellent stability and compatibility with diverse reaction conditions. This reagent facilitates efficient C–C bond formation in late-stage functionalization and heterocyclic scaffold elaboration, offering reliable yields and straightforward purification.

Safety Information

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GHS Pictogram :
GHS No : GHS06,GHS08,GHS09
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H315-H317-H319-H330-H334-H335-H370-H410
Precautionary Statements : P260-P261-P264-P270-P271-P272-P273-P280-P284-P302+P352-P304+P340-P362+P364-P391-P405-P501

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Computational Chemistry Data

  • TPSA   51.66
  • LogP   1.0826
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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