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CS-W001157 4
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2-Chloropyridine-5-boronic acid

  • CAS No. 444120-91-6

  • Cat. No. CS-W019734
  • Purity≥97%
  • MDL No.MFCD03094998

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

2-Chloropyridine-5-boronic acid|CS-W019734

Structure of 444120-91-6

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General Information

  • CAS No. 444120-91-6
  • Cat. No. CS-W019734
  • Purity ≥97%
  • MDL No. MFCD03094998
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BClNO₂
  • Molecular Weight 157.36
  • Synonym(s) None
  • SMILES ClC1=CC=C(B(O)O)C=N1

Description

6-Chloro-3-pyridinylboronic acid can be used:To prepare biologically significant 3-arylcoumarins by reacting with 3-chlorocoumarin through Suzuki reaction.As a substrate in the synthesis of 11-(pyridinylphenyl)steroid with progesterone agonist/antagonist profile.As a substrate in the preparation of - secondary and tertiary pyridines by the reaction of pyridotriazoles with boronic acids.As a substrate in the palladium-catalyzed -arylation of saturated cyclic amines and N-methyl amines.

Application

2-Chloropyridine-5-boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation with aryl and vinyl halides. Its stability under ambient conditions and compatibility with diverse functional groups facilitate straightforward synthesis of substituted pyridines. The pendant boronic acid moiety allows for reliable coupling, while the chlorine substituent provides orthogonal reactivity for sequential transformations. This compound is particularly valuable in constructing biologically relevant heterocyclic scaffolds.

Synthesis

  • Route1

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 14 p. 2885 - 2890
  • Route2
    • In-stock
      5-Bromo-2-chloropyridine|CS-W002767
      53939-30-3
    • ~%
    • null|null
      11113-50-1
    • In-stock
      2-Chloropyridine-5-boronic acid|CS-W019734
      444120-91-6

    References

    • XENON PHARMACEUTICALS INC. Patent: WO2006/34440 A2, 2006 ; Location in patent: Page/Page column 48 ; WO 2006/034440 A2
  • Route3

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 14 p. 2885 - 2890

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

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Computational Chemistry Data

  • TPSA   53.35
  • LogP   -0.5852
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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