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CS-W001157 4
Total: USD 88.00

2-Chloropyridine-3-boronic acid

  • CAS No. 381248-04-0

  • Cat. No. CS-D1047
  • Purity≥98%
  • MDL No.MFCD03094997

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

2-Chloropyridine-3-boronic acid|CS-D1047

Structure of 381248-04-0

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General Information

  • CAS No. 381248-04-0
  • Cat. No. CS-D1047
  • Purity ≥98%
  • MDL No. MFCD03094997
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BClNO₂
  • Molecular Weight 157.36
  • Synonym(s) None
  • SMILES ClC1=NC=CC=C1B(O)O

Description

2-Chloropyridine-3-boronic acid features a boronic acid group positioned ortho to a chlorine atom on a pyridine ring, enabling direct functionalization in cross-coupling reactions. This configuration enhances reactivity in Suzuki-Miyaura processes while maintaining stability under standard conditions. The electron-deficient pyridine ring facilitates controlled coupling with diverse aryl and heteroaryl partners.

Application

2-Chloropyridine-3-boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation with aryl and heteroaryl halides. The boronic acid functionality exhibits good bench stability and compatibility with diverse reaction conditions, while the ortho-chloropyridine moiety provides a handle for further functionalization via palladium-catalyzed transformations. Its predictable reactivity and ease of purification make it a practical choice for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R.; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 17 p. 3323 - 3328
  • Route2
    • null|null
      109-09-1
    • ~61%
    • In-stock
      2-Chloropyridine-3-boronic acid|CS-D1047
      381248-04-0

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R.; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 17 p. 3323 - 3328
  • Route3

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R.; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 17 p. 3323 - 3328

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-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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