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4,4,5,5-Tetramethyl-2-(thieno[3,2-b]thiophen-2-yl)-1,3,2-dioxaborolane

  • CAS No. 1004784-50-2

  • Cat. No. CS-0438327
  • Purity≥98%
  • MDL No.None

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

4,4,5,5-Tetramethyl-2-(thieno[3,2-b]thiophen-2-yl)-1,3,2-dioxaborolane|CS-0438327

Structure of 1004784-50-2

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General Information

  • CAS No. 1004784-50-2
  • Cat. No. CS-0438327
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅BO₂S₂
  • Molecular Weight 266.19
  • Synonym(s) 4,4,5,5-tetramethyl-2-thieno[3,2-b]thiophen-2-yl-[1,3,2]dioxaborolane
  • SMILES CC1(C)OB(C2=CC3=C(C=CS3)S2)OC1(C)C

Description

This boronate ester integrates a thieno[3,2-b]thiophene unit with high thermal stability and enhanced solubility in organic solvents. The tetramethyl-substituted dioxaborolane ring ensures excellent shelf life and resistance to hydrolysis under standard conditions. It enables efficient Suzuki-Miyaura couplings with minimal protodeboronation, delivering precise C–C bond formation in complex heterocyclic systems.

Application

4,4,5,5-Tetramethyl-2-(thieno[3,2-b]thiophen-2-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The thieno[3,2-b]thiophene moiety imparts enhanced electronic properties and metabolic stability, making it particularly useful in the synthesis of conjugated materials and functionalized heterocycles. Its high functional group tolerance and ease of purification enable reliable integration into complex molecular architectures.

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-P330-P362-P405-P501

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.262
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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