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CS-W001157 4
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4,4,5,5-Tetramethyl-2-(4-(methylsulfonyl)phenyl)-1,3,2-dioxaborolane

  • CAS No. 603143-27-7

  • Cat. No. CS-M1424
  • Purity≥98%
  • MDL No.MFCD05863921

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

4,4,5,5-Tetramethyl-2-(4-(methylsulfonyl)phenyl)-1,3,2-dioxaborolane|CS-M1424

Structure of 603143-27-7

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General Information

  • CAS No. 603143-27-7
  • Cat. No. CS-M1424
  • Purity ≥98%
  • MDL No. MFCD05863921
  • Storage 4°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BO₄S
  • Molecular Weight 282.16
  • Synonym(s) 4-Methylsulfonylphenylboronic acid,pinacol ester
  • SMILES O=S(C1=CC=C(C=C1)B2OC(C)(C(C)(O2)C)C)(C)=O

Description

This boronate ester features a methylsulfonyl-substituted phenyl ring and tetramethyl-substituted dioxaborolane, delivering enhanced stability and solubility. It integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions, enabling efficient construction of biaryl architectures with minimal decomposition.

Application

4,4,5,5-Tetramethyl-2-(4-(methylsulfonyl)phenyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The methylsulfonyl group enhances solubility and provides orthogonal reactivity in multi-step syntheses. Its tetramethyl-substituted dioxaborolane core ensures high chemical stability, minimal protodeboronation, and compatibility with diverse reaction conditions, enabling efficient construction of biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Li, Pengbin; Fu, Chunling; Ma, Shengming Organic and Biomolecular Chemistry, 2014 , vol. 12, # 22 p. 3604 - 3610

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   52.6
  • LogP   1.3893
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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