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

  • CAS No. 676501-85-2

  • Cat. No. CS-0112641
  • Purity≥97%
  • MDL No.MFCD09952061

*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-2-carbonitrile|CS-0112641

Structure of 676501-85-2

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General Information

  • CAS No. 676501-85-2
  • Cat. No. CS-0112641
  • Purity ≥97%
  • MDL No. MFCD09952061
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₄BNO₂S
  • Molecular Weight 235.11
  • Synonym(s) 5-CYANOTHIOPHENE-2-BORONIC ACID PINACOL ESTER
  • SMILES N#CC1=CC=C(B2OC(C)(C)C(C)(C)O2)S1

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile features a boronate ester group coupled with an electron-deficient thiophene core bearing a nitrile. This combination enables efficient palladium-catalyzed cross-coupling reactions under mild conditions, delivering functionalized heteroaryl architectures with high stability and predictable reactivity in synthetic workflows.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylborolane moiety enables stable, air-tolerant handling and broad functional group compatibility. It facilitates efficient construction of biaryl and heteroaryl scaffolds, particularly in the synthesis of conjugated materials and medicinally relevant thienyl derivatives.

Safety Information

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GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H319
Precautionary Statements : P264-P270-P330-P405-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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