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CS-W001157 4
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2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

  • CAS No. 444120-94-9

  • Cat. No. CS-W003058
  • Purity≥95%
  • MDL No.MFCD03412793

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

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W003058

Structure of 444120-94-9

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General Information

  • CAS No. 444120-94-9
  • Cat. No. CS-W003058
  • Purity ≥95%
  • MDL No. MFCD03412793
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₅BClNO₂
  • Molecular Weight None
  • Synonym(s) 2-Chloropyridine-5-boronicacidpinacolester
  • SMILES CC(C(C)(O1)C)(OB1C2=CN=C(Cl)C=C2)C

Description

This boronate-functionalized pyridine integrates readily into Suzuki-Miyaura coupling reactions under standard conditions. The tetramethylboronate moiety enhances stability and reactivity, while the chloropyridine handle enables selective cross-coupling with minimal side-product formation.

Application

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile Suzuki-Miyaura coupling partner, enabling efficient C–C bond formation under mild conditions. The boronate group exhibits high stability, excellent functional group tolerance, and compatibility with diverse reaction partners. Its pyridine core facilitates integration into bioactive heterocycles, while the chloro substituent supports sequential cross-coupling or further derivatization in medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 14 p. 2885 - 2890
  • Route2

    References

    • Watson, Charlotte G.; Aggarwal, Varinder K. Organic Letters, 2013 , vol. 15, # 6 p. 1346 - 1349
  • 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 : H319
Precautionary Statements : P264-P280-P305+P351+P338-P337+P313

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Computational Chemistry Data

  • TPSA   31.35
  • LogP   2.0342
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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