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CS-W001157 4
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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde

  • CAS No. 848093-29-8

  • Cat. No. CS-0041776
  • Purity≥98%
  • MDL No.MFCD04038759

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde|CS-0041776

Structure of 848093-29-8

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General Information

  • CAS No. 848093-29-8
  • Cat. No. CS-0041776
  • Purity ≥98%
  • MDL No. MFCD04038759
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆BNO₃
  • Molecular Weight 233.07
  • Synonym(s) 5-Formylpyridine-3-boronic acid pinacol ester
  • SMILES O=CC1=CN=CC(B2OC(C)(C)C(C)(C)O2)=C1

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde features a boronate ester group fused to a pyridine aldehyde scaffold, enabling direct incorporation into Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety imparts enhanced stability and moisture tolerance, while the aldehyde functionality offers a handle for downstream derivatization. This reagent streamlines access to complex heteroaryl aldehydes under standard conditions.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The aldehyde functionality enables direct functionalization or derivatization, while the stable boronate ester facilitates mild reaction conditions and excellent functional group tolerance. Its bench-stable nature and compatibility with diverse substrates make it ideal for constructing complex heterocyclic scaffolds and 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-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   48.42
  • LogP   1.1933
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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