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2-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

  • CAS No. 1350933-21-9

  • Cat. No. CS-0135449
  • Purity≥95%
  • MDL No.MFCD16994359

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

2-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile|CS-0135449

Structure of 1350933-21-9

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General Information

  • CAS No. 1350933-21-9
  • Cat. No. CS-0135449
  • Purity ≥95%
  • MDL No. MFCD16994359
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆BNO₃
  • Molecular Weight 245.08
  • Synonym(s) benzonitrile,2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
  • SMILES N#CC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1O

Description

This boronate ester features a para-cyano group flanked by a phenolic hydroxyl, enabling dual functionality in cross-coupling and derivatization. The tetramethyl-substituted dioxaborolane enhances stability and reactivity under standard conditions, facilitating efficient Suzuki-Miyaura coupling with minimal decomposition.

Application

2-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile serves as a versatile boronate ester building block for Suzuki-Miyaura cross-coupling reactions. The ortho-hydroxyl and nitrile groups provide orthogonal functionality for further derivatization, while the pinacol boronate moiety ensures excellent stability, ease of handling, and compatibility with a broad range of reaction conditions. This compound enables efficient construction of biaryl and heterocyclic scaffolds in 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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   62.48
  • LogP   1.56308
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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