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CS-W001157 4
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(5-Cyanobenzo[b]thiophen-2-yl)boronic acid

  • CAS No. 1142946-81-3

  • Cat. No. CS-0441115
  • Purity≥96%
  • MDL No.None

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

(5-Cyanobenzo[b]thiophen-2-yl)boronic acid|CS-0441115

Structure of 1142946-81-3

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General Information

  • CAS No. 1142946-81-3
  • Cat. No. CS-0441115
  • Purity ≥96%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BNO₂S
  • Molecular Weight 203.03
  • Synonym(s) 5-cyanobenzo[b]thiophen-2-ylboronic acid
  • SMILES C1=CC2=C(C=C1C#N)C=C(B(O)O)S2

Description

This boronate moiety features a cyanated benzo[b]thiophene scaffold, delivering enhanced electronic tuning and stability. The para-cyano group imparts strong electron-withdrawing character, enabling efficient cross-coupling under standard conditions. Bench-stable and moisture-tolerant, it integrates seamlessly into complex molecular architectures.

Application

(5-Cyanobenzo[b]thiophen-2-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The cyanide group enhances electrophilicity for downstream functionalization, while the boronic acid moiety offers excellent bench stability and compatibility with diverse reaction conditions. Its orthogonality to common protecting groups facilitates modular synthesis of complex scaffolds in medicinal chemistry and materials science.

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   64.25
  • LogP   0.45278
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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