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6-(Benzyloxy)pyridine-3-boronic Acid

  • CAS No. 929250-35-1

  • Cat. No. CS-0156152
  • Purity≥98%
  • MDL No.MFCD06798262

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

6-(Benzyloxy)pyridine-3-boronic Acid|CS-0156152

Structure of 929250-35-1

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General Information

  • CAS No. 929250-35-1
  • Cat. No. CS-0156152
  • Purity ≥98%
  • MDL No. MFCD06798262
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₂BNO₃
  • Molecular Weight 229.04
  • Synonym(s) 6-Benzyloxypyridine-3-boronic acid
  • SMILES C1=CC=C(C=C1)COC2=NC=C(C=C2)B(O)O

Description

6-(Benzyloxy)pyridine-3-boronic acid integrates a pyridine scaffold with a boronic acid and benzyloxy handle, enabling direct coupling in Suzuki-Miyaura reactions. The electron-deficient pyridine ring enhances reactivity, while the benzyl ether protects the hydroxyl during synthesis. This bench-stable derivative delivers efficient access to functionalized heterocycles under standard conditions.

Application

6-(Benzyloxy)pyridine-3-boronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. The pyridine scaffold provides strong coordination to transition metals, while the benzyloxy group offers orthogonal stability and convenient removal via acidolysis. Its boronic acid functionality enables reliable coupling with aryl and vinyl halides, facilitating access to complex heterocyclic architectures commonly found in pharmaceutical intermediates. Bench-stable and amenable to standard purification protocols, it functions effectively in multi-step synthetic sequences.

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   62.58
  • LogP   0.3404
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   4

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