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CS-W001157 4
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N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide

  • CAS No. 904326-87-0

  • Cat. No. CS-0091618
  • Purity≥98%
  • MDL No.MFCD08690229

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

N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide|CS-0091618

Structure of 904326-87-0

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General Information

  • CAS No. 904326-87-0
  • Cat. No. CS-0091618
  • Purity ≥98%
  • MDL No. MFCD08690229
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BN₂O₃
  • Molecular Weight 262.11
  • Synonym(s) N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide
  • SMILES CC(NC1=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1)=O

Description

N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide features a pyridine-linked boronate ester enabling efficient Suzuki-Miyaura cross-coupling under mild conditions. The acetyl group enhances solubility and stability, while the tetramethyl-substituted dioxaborolane resists hydrolysis. This bench-stable reagent integrates seamlessly into late-stage functionalization workflows for heterocyclic scaffolds.

Application

N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyridine scaffold enables transition metal-catalyzed C–C bond formation with aryl, heteroaryl, and vinyl halides under mild conditions. Its stability, ease of handling, and compatibility with diverse functional groups make it ideal for constructing biaryl and heterocyclic architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • In-stock
      5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine|CS-W000973
      827614-64-2
    • null|null
      108-24-7
    • ~61%
    • In-stock
      N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide|CS-0091618
      904326-87-0

    References

    • EP2719697 A1, ; Paragraph 0152-0154 ;
  • Route2

    References

    • WO2006/79791 A1, ; Page/Page column 42 ; WO 2006/079791 A1
  • Route3

    References

    • US2014/93505 A1, ; Page/Page column ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   60.45
  • LogP   1.3392
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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