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

  • CAS No. 2096331-60-9

  • Cat. No. CS-0161072
  • Purity≥97%
  • MDL No.MFCD11975320

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

3-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|CS-0161072

Structure of 2096331-60-9

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General Information

  • CAS No. 2096331-60-9
  • Cat. No. CS-0161072
  • Purity ≥97%
  • MDL No. MFCD11975320
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₅BN₂O₄
  • Molecular Weight 250.06
  • Synonym(s) None
  • SMILES CC1(C)C(C)(C)OB(C2=CN=CC([N+]([O-])=O)=C2)O1

Description

3-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester group paired with an electron-deficient pyridine ring, enabling efficient Suzuki-Miyaura coupling under standard conditions. This bench-stable reagent integrates readily into complex molecule assembly, offering reliable functionalization at the 5-position.

Application

3-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The nitropyridine motif provides enhanced electrophilicity and facilitates downstream functionalization, while the tetramethylboronate group ensures excellent stability, low toxicity, and compatibility with aqueous workups. Its orthogonality to common functional groups enables efficient late-stage diversification in heterocyclic synthesis, making it a reliable scaffold for medicinal chemistry and materials science applications.

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   74.49
  • LogP   1.289
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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