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CS-W001157 4
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[6-(Dimethylamino)pyridin-3-yl]boronic acid

  • CAS No. 579525-46-5

  • Cat. No. CS-W005756
  • Purity≥95%
  • MDL No.MFCD06409949

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

[6-(Dimethylamino)pyridin-3-yl]boronic acid|CS-W005756

Structure of 579525-46-5

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General Information

  • CAS No. 579525-46-5
  • Cat. No. CS-W005756
  • Purity ≥95%
  • MDL No. MFCD06409949
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₁BN₂O₂
  • Molecular Weight 165.99
  • Synonym(s) 6-(Dimethylamino)pyridine-3-boronic acid
  • SMILES CN(C1=CC=C(C=N1)B(O)O)C

Description

This boronate moiety integrates a dimethylamino-pyridine handle, enhancing both solubility and reactivity in Suzuki-Miyaura coupling. The electron-rich pyridine ring facilitates rapid transmetalation, while the stable boronic acid functionality enables efficient cross-coupling under mild conditions.

Application

[6-(Dimethylamino)pyridin-3-yl]boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl architectures. The electron-rich dimethylaminopyridine moiety enhances reactivity while maintaining bench stability and compatibility with diverse functional groups. Its utility extends to the synthesis of pharmaceutical intermediates and functional materials, offering predictable coupling efficiency and straightforward purification.

Synthesis

  • Route1
    • In-stock
      2-Pyridinamine, 5-bromo-N,N-dimethyl-|CS-0030447
      26163-07-5
    • null|null
      5419-55-6
    • ~%
    • In-stock
      [6-(Dimethylamino)pyridin-3-yl]boronic acid|CS-W005756
      579525-46-5

    References

    • Advanced Synthesis and Catalysis, , vol. 345, # 5 p. 620 - 624
  • Route2

    References

    • WO2012/167423 A1, ; WO 2012/167423 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   56.59
  • LogP   -1.1726
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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