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4,4,5,5-Tetramethyl-2-(5-methylthiophen-3-yl)-1,3,2-dioxaborolane

  • CAS No. 874959-74-7

  • Cat. No. CS-0096071
  • Purity≥95%
  • MDL No.MFCD18383149

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

4,4,5,5-Tetramethyl-2-(5-methylthiophen-3-yl)-1,3,2-dioxaborolane|CS-0096071

Structure of 874959-74-7

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General Information

  • CAS No. 874959-74-7
  • Cat. No. CS-0096071
  • Purity ≥95%
  • MDL No. MFCD18383149
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇BO₂S
  • Molecular Weight 224.13
  • Synonym(s) 4,4,5,5-tetramethyl-2-(5-methyl-3-thienyl)-1,3,2-dioxaborolane
  • SMILES CC1=CC(B2OC(C)(C)C(C)(C)O2)=CS1

Description

This boronate ester features a sterically hindered tetramethyl-1,3,2-dioxaborolane core paired with a 5-methylthiophen-3-yl group, delivering enhanced stability and reactivity in cross-coupling processes. The electron-rich thiophene moiety facilitates efficient palladium-catalyzed transformations under mild conditions.

Application

4,4,5,5-Tetramethyl-2-(5-methylthiophen-3-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane enhances air and moisture stability while maintaining high reactivity in palladium-catalyzed transformations. It facilitates efficient coupling with aryl and heteroaryl halides, enabling rapid construction of biaryl and thiophene-containing scaffolds common in pharmaceutical and materials chemistry.

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-P363-P501

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.35572
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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