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2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

  • CAS No. 1034297-69-2

  • Cat. No. CS-0041735
  • Purity≥95%
  • MDL No.MFCD06798266

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

2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0041735

Structure of 1034297-69-2

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General Information

  • CAS No. 1034297-69-2
  • Cat. No. CS-0041735
  • Purity ≥95%
  • MDL No. MFCD06798266
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₈BNO₃
  • Molecular Weight 235.09
  • Synonym(s) 6-Methoxypyridine-2-Boronic Acid Pinacol Ester
  • SMILES COC1=NC(=CC=C1)B1OC(C)(C)C(C)(C)O1

Description

2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group flanked by a methoxy-substituted pyridine ring, enabling efficient Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and reactivity, while the electron-rich pyridine core facilitates selective functionalization. This compound serves as a robust building block for conjugated materials and bioactive heterocycles.

Application

2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pinacol boronate group enables stable, air-tolerant handling and facilitates efficient C–C bond formation with aryl, heteroaryl, and vinyl halides under mild conditions. Its methoxy substituent provides electronic modulation and enhances solubility, supporting broad functional group tolerance and compatibility in complex molecule synthesis. This reagent functions reliably in both small-molecule discovery and process chemistry workflows.

Synthesis

  • Route1

    References

    • WO2008/74997 A1, ; Page/Page column 88 ; WO 2008/074997 A1

Safety Information

Download SDS
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   1.3894
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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