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

  • CAS No. 458532-84-8

  • Cat. No. CS-W000937
  • Purity≥98%
  • MDL No.MFCD04039870

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

2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-W000937

Structure of 458532-84-8

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General Information

  • CAS No. 458532-84-8
  • Cat. No. CS-W000937
  • Purity ≥98%
  • MDL No. MFCD04039870
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₅BClNO₂
  • Molecular Weight None
  • Synonym(s) 2-Chloropyridine-4-boronic Acid Pinacol Ester
  • SMILES CC(C(C)(O1)C)(OB1C2=CC(Cl)=NC=C2)C

Description

2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety enhances stability and reactivity under standard conditions. This pyridine derivative serves as a key building block for functionalized heterocycles in medicinal chemistry and materials science applications.

Application

2-Chloro-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 group exhibits excellent stability, tolerates diverse functional groups, and facilitates rapid purification. Its pyridine scaffold provides a valuable building block for constructing bioactive heterocycles, pharmaceutical intermediates, and conjugated materials in medicinal chemistry and materials science workflows.

Synthesis

  • Route1

    References

    • Bouillon, Alexandre; Lancelot, Jean-Charles; Collot, Valerie; Bovy, Philippe R; Rault, Sylvain Tetrahedron, 2002 , vol. 58, # 22 p. 4369 - 4373
  • Route2

    References

    • Watson, Charlotte G.; Aggarwal, Varinder K. Organic Letters, 2013 , vol. 15, # 6 p. 1346 - 1349
  • Route3

    References

    • Wang, Lianhui; Cui, Xiuling; Li, Jingya; Wu, Yusheng; Zhu, Zhiwu; Wu, Yangjie European Journal of Organic Chemistry, 2012 , # 3 p. 595 - 603

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H320
Precautionary Statements : P264-P270-P301+P310-P305+P351+P338-P330-P337+P313-P405-P501

Quality Control

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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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