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CS-W001157 4
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(5-(Trifluoromethyl)pyridin-3-yl)boronic acid

  • CAS No. 947533-51-9

  • Cat. No. CS-0054394
  • Purity≥95%
  • MDL No.None

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

(5-(Trifluoromethyl)pyridin-3-yl)boronic acid|CS-0054394

Structure of 947533-51-9

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General Information

  • CAS No. 947533-51-9
  • Cat. No. CS-0054394
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BF₃NO₂
  • Molecular Weight 190.92
  • Synonym(s) BP 33117 5-TRIFLUOROMETHYL-PYRIDINE-3-BORONIC ACID
  • SMILES OB(O)C1=CC(=CN=C1)C(F)(F)F

Description

This boronate moiety features a trifluoromethyl group at the pyridine 5-position, enhancing electron deficiency and stability. It integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions, delivering functionalized heteroaryl products with high efficiency and minimal decomposition.

Application

(5-(Trifluoromethyl)pyridin-3-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. Its trifluoromethyl group enhances metabolic stability and modulates electronic properties, while the boronic acid functionality provides excellent bench stability and compatibility with diverse reaction conditions. Functions reliably in late-stage functionalization and API scaffold synthesis.

Synthesis

  • Route1

    References

    • Clapham, Kate M.; Batsanov, Andrei S.; Bryce, Martin R.; Tarbit, Brian Organic and Biomolecular Chemistry, 2009 , vol. 7, # 10 p. 2155 - 2161
  • Route2

    References

    • WO2012/3283 A1, ; Page/Page column 239 ; WO 2012/003283 A1
  • Route3
    • null|null
      5419-55-6
    • In-stock
      3-Bromo-5-(trifluoromethyl)pyridine|CS-W007687
      436799-33-6
    • ~93%
    • In-stock
      (5-(Trifluoromethyl)pyridin-3-yl)boronic acid|CS-0054394
      947533-51-9

    References

    • Jacobus Pharmaceutical Company, Inc.; Heffernan, Gavin David; Jacobus, David Penman; Saionz, Kurt William; Schiehser, Guy Alan; Shieh, Hong-Ming; Zhao, Wenyi Patent: US2014/135320 A1, 2014 ; Location in patent: Paragraph 0224; 0225 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   53.35
  • LogP   -0.2198
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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