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CS-W001157 4
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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2-((trimethylsilyl)oxy)propan-2-yl)pyridine

  • CAS No. 1228014-10-5

  • Cat. No. CS-W019249
  • Purity≥97%
  • MDL No.MFCD12198135

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2-((trimethylsilyl)oxy)propan-2-yl)pyridine|CS-W019249

Structure of 1228014-10-5

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General Information

  • CAS No. 1228014-10-5
  • Cat. No. CS-W019249
  • Purity ≥97%
  • MDL No. MFCD12198135
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₃₀BNO₃Si
  • Molecular Weight 335.32
  • Synonym(s) 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-{2-[(trimethylsilyl)oxy]-2-propanyl}pyridine
  • SMILES CC(C1=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1)(O[Si](C)(C)C)C

Description

This boronate-functionalized pyridine integrates a tetramethylboronate group and a silyl-protected alcohol, enabling stable coupling in Suzuki-Miyaura reactions. The trimethylsilyl ether offers enhanced stability during storage and handling, while the para-substituted pyridine serves as a robust directing group in transition metal catalysis.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2-((trimethylsilyl)oxy)propan-2-yl)pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient palladium-catalyzed coupling under mild conditions, while the silyl ether-protected hydroxyl functionality offers orthogonal stability and selective deprotection. This dual-functional design facilitates modular synthesis of complex pyridine-based scaffolds with excellent bench stability and compatibility in multi-step sequences.

Safety Information

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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   40.58
  • LogP   3.4674
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   4

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