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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbonitrile

  • CAS No. 916454-59-6

  • Cat. No. CS-0246086
  • Purity≥98%
  • MDL No.None

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbonitrile|CS-0246086

Structure of 916454-59-6

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General Information

  • CAS No. 916454-59-6
  • Cat. No. CS-0246086
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₄BNO₂S
  • Molecular Weight 235.11
  • Synonym(s) 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbo
  • SMILES CC1(C)C(C)(C)OB(C2=CC(=CS2)C#N)O1

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbonitrile features a boronate ester group coupled with an electron-deficient thiophene core bearing a nitrile substituent. This combination enables efficient Suzuki-Miyaura coupling under mild conditions while maintaining bench-stable handling and enhanced solubility in polar organic solvents.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbonitrile serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the nitrile functionality provides orthogonal reactivity for downstream modifications. Bench-stable and readily purified by flash chromatography, it facilitates the construction of complex thiophene-based scaffolds common 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-H315-H319
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   42.25
  • LogP   1.91898
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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