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2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

  • CAS No. 876922-75-7

  • Cat. No. CS-0108810
  • Molecule weight269.15
  • Purity≥98%
  • MDL No.MFCD22418301

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

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline|CS-0108810

Structure of 876922-75-7

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General Information

  • CAS No. 876922-75-7
  • Cat. No. CS-0108810
  • Purity ≥98%
  • MDL No. MFCD22418301
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₀BNO₂
  • Molecular Weight 269.15
  • Synonym(s) 2-Methyl-quinoline-5-boronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=C3C=CC(C)=NC3=CC=C2)O1

Description

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline is a bench-stable boronate reagent featuring a sterically protected boryl group attached to a quinoline scaffold. This configuration enables efficient Suzuki-Miyaura cross-coupling under mild conditions, delivering functionalized quinoline derivatives with high regioselectivity and minimal protodeboronation.

Application

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline serves as a robust boronate building block for palladium-catalyzed cross-coupling reactions. Its quinoline scaffold offers enhanced stability and favorable electronic properties, enabling efficient Suzuki-Miyaura coupling with aryl, vinyl, and heteroaryl halides. The tetramethylboronate group ensures excellent shelf life, low toxicity, and ease of purification, making it ideal for modular synthesis of biologically relevant heterocycles and advanced pharmaceutical intermediates.

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-H320-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

  • TPSA   31.35
  • LogP   2.84242
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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