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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,5-a]pyridine

  • CAS No. 1445860-57-0

  • Cat. No. CS-0040530
  • Purity≥97%
  • MDL No.None

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

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,5-a]pyridine|CS-0040530

Structure of 1445860-57-0

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General Information

  • CAS No. 1445860-57-0
  • Cat. No. CS-0040530
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇BN₂O₂
  • Molecular Weight 244.10
  • Synonym(s) Imidazo[1,5-a]pyridine-6-boronic Acid Pinacol Ester
  • SMILES CC1(C)C(C)(C)OB(C2=CN3C(C=C2)=CN=C3)O1

Description

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,5-a]pyridine is a bench-stable boronate ester featuring a rigid imidazo[1,5-a]pyridine core. This structure integrates seamlessly into Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. The tetramethylcyclopentadienyl moiety enhances stability and solubility in organic media.

Application

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,5-a]pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety offers excellent stability under ambient conditions and facilitates efficient coupling with aryl and heteroaryl halides. Its imidazo[1,5-a]pyridine core provides a privileged scaffold in medicinal chemistry, enabling rapid access to biologically active molecules through modular synthesis. Functions reliably in diverse reaction conditions with high functional group tolerance and ease of purification.

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   35.76
  • LogP   1.6335
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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