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CS-W001157 4
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4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole

  • CAS No. 1088118-97-1

  • Cat. No. CS-0177137
  • Purity≥95%
  • MDL No.None

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

4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole|CS-0177137

Structure of 1088118-97-1

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General Information

  • CAS No. 1088118-97-1
  • Cat. No. CS-0177137
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅BN₂O₂S
  • Molecular Weight 262.14
  • Synonym(s) 4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole
  • SMILES CC1(C)OB(C2=CC=CC3=NSN=C32)OC1(C)C

Description

4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole features a boronate ester group enabling facile Suzuki-Miyaura coupling, paired with a rigid benzothiadiazole core that imparts strong electron-withdrawing character and enhanced photostability. This combination facilitates efficient incorporation into conjugated molecular architectures for optoelectronic materials and functionalized heterocycles.

Application

4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient C–C bond formation under mild conditions, offering excellent stability and ease of handling. It functions reliably in the synthesis of biaryl architectures and functionalized heterocycles, with broad compatibility across diverse reaction substrates. Its robustness and predictable reactivity make it a practical choice for constructing complex molecular scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Anant, Piyush; Lucas, Nigel T.; Jacob, Josemon Organic Letters, 2008 , vol. 10, # 24 p. 5533 - 5536

Safety Information

Download SDS
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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   44.24
  • LogP   1.9905
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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