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

  • CAS No. 1073354-99-0

  • Cat. No. CS-W006007
  • Purity≥97%
  • MDL No.MFCD09260489

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine|CS-W006007

Structure of 1073354-99-0

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General Information

  • CAS No. 1073354-99-0
  • Cat. No. CS-W006007
  • Purity ≥97%
  • MDL No. MFCD09260489
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇BN₂O₂
  • Molecular Weight 220.08
  • Synonym(s) 3-Aminopyridine-5-Boronic Acid, Pinacol Ester
  • SMILES NC1=CN=CC(B(OC2(C)C)OC2(C)C)=C1

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine features a boronate ester group paired with a pyridine-3-amine scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent integrates readily into complex molecule assembly, offering high functional group tolerance and reliable coupling efficiency in diverse synthetic workflows.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyridin-3-amine moiety provides a handle for further functionalization, while the pinacol boronate ester ensures excellent bench stability and compatibility with diverse reaction conditions. Its ortho-directing nitrogen enables efficient coupling with aryl halides and pseudohalides, facilitating rapid access to biaryl scaffolds prevalent in pharmaceutical and agrochemical development.

Synthesis

  • Route1

    References

    • WO2013/126608 A1, ; Paragraph 00394 ;

Safety Information

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GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   57.37
  • LogP   0.963
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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