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CS-W001157 4
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4,4,5,5-Tetramethyl-2-pyren-1-yl-1,3,2-dioxaborolane

  • CAS No. 349666-24-6

  • Cat. No. CS-0061091
  • Purity≥97%
  • MDL No.None

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

4,4,5,5-Tetramethyl-2-pyren-1-yl-1,3,2-dioxaborolane|CS-0061091

Structure of 349666-24-6

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General Information

  • CAS No. 349666-24-6
  • Cat. No. CS-0061091
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₂H₂₁BO₂
  • Molecular Weight 328.21
  • Synonym(s) 4,4,5,5-Tetramethyl-2-(pyren-1-YL)-1,3,2-dioxaborolane
  • SMILES CC1(C)C(C)(C)OB(C2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2)O1

Description

This tetramethyl-substituted pyrenyl boronate features a sterically protected boronate ester that enhances stability and shelf life. The electron-rich pyrene moiety enables efficient coupling in Suzuki-Miyaura reactions, delivering high yields with minimal protodeboronation. This bench-stable reagent simplifies the synthesis of complex conjugated systems and functionalized aryl scaffolds under standard conditions.

Application

4,4,5,5-Tetramethyl-2-pyren-1-yl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its pyrenyl group provides enhanced π-conjugation and thermal stability, enabling efficient coupling with aryl and heteroaryl halides under mild conditions. The tetramethyl-substituted dioxaborolane core ensures excellent shelf life, low hydrolytic sensitivity, and straightforward purification, making it ideal for constructing complex polycyclic aromatic scaffolds in materials science and pharmaceutical research.

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   18.46
  • LogP   4.8832
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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