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2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

  • CAS No. 652148-92-0

  • Cat. No. CS-0040321
  • Purity≥95%
  • MDL No.MFCD06798259

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

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0040321

Structure of 652148-92-0

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General Information

  • CAS No. 652148-92-0
  • Cat. No. CS-0040321
  • Purity ≥95%
  • MDL No. MFCD06798259
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₅BClNO₂
  • Molecular Weight 239.51
  • Synonym(s) 6-CHLOROPYRIDINE-2-BORONIC ACID PINACOL ESTER
  • SMILES CC1(C)C(C)(C)OB(C2=CC=CC(Cl)=N2)O1

Description

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling under mild conditions. The electron-deficient pyridine ring enhances reactivity in palladium-catalyzed transformations. This bench-stable reagent integrates seamlessly into complex molecular architectures with high functional group tolerance.

Application

2-Chloro-6-(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. This reagent facilitates the construction of biaryl architectures in medicinal chemistry and materials science workflows, offering reliable performance and straightforward purification.

Synthesis

  • Route1

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Santos, Jana Sopkova De Oliveira; Collot, Valerie; Bovy, Philipppe R.; Rault, Sylvain Tetrahedron, 2003 , vol. 59, # 50 p. 10043 - 10049
  • Route2

    References

    • Tetrahedron, , vol. 59, # 50 p. 10043 - 10049

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

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