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6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

  • CAS No. 944401-67-6

  • Cat. No. CS-0061090
  • Molecule weight238.07
  • Purity≥95%
  • MDL No.MFCD12923416

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

6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine|CS-0061090

Structure of 944401-67-6

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General Information

  • CAS No. 944401-67-6
  • Cat. No. CS-0061090
  • Purity ≥95%
  • MDL No. MFCD12923416
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₆BFN₂O₂
  • Molecular Weight 238.07
  • Synonym(s) 6-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-imine
  • SMILES NC1=NC(F)=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine integrates a boronate ester and an amine group on a fluorinated pyridine scaffold. This bifunctional building block enables efficient Suzuki-Miyaura coupling and direct derivatization under standard conditions, offering enhanced stability and compatibility in complex synthesis workflows.

Application

6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. The pyridine core enables access to biologically relevant scaffolds, while the pinacol boronate group offers excellent stability, ease of handling, and compatibility with diverse reaction conditions. Functional group tolerance supports efficient late-stage functionalization in medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi Patent: WO2012/109423 A1, 2012 ; Location in patent: Page/Page column 24 ;
  • Route2

    References

    • WO2012/109423 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   57.37
  • LogP   1.1021
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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