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

  • CAS No. 697739-24-5

  • Cat. No. CS-0145685
  • Molecule weight269.53
  • Purity≥98%
  • MDL No.None

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

2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0145685

Structure of 697739-24-5

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General Information

  • CAS No. 697739-24-5
  • Cat. No. CS-0145685
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₇BClNO₃
  • Molecular Weight 269.53
  • Synonym(s) 2-CHLORO-6-METHOXYPYRIDINE-4-BORONIC ACID PINACOL ESTER
  • SMILES COC1=CC(B(O2)OC(C)(C)C2(C)C)=CC(Cl)=N1

Description

2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group enabling efficient Suzuki-Miyaura coupling under mild conditions. The electron-deficient pyridine core enhances reactivity, while the methoxy substituent improves solubility and stability. This bench-stable reagent streamlines access to functionalized heterocycles in medicinal chemistry and materials synthesis.

Application

2-Chloro-6-methoxy-4-(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 ester group exhibits excellent stability and functional group tolerance, while the chloropyridine moiety facilitates selective cross-coupling with aryl, heteroaryl, and vinyl partners. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical building block for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Zeqing, Li; Zhibin, Liang; Yuqiang, Wang; Pei, Yu Research on Chemical Intermediates, 2013 , vol. 39, # 4 p. 1917 - 1926

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   40.58
  • LogP   2.0428
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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