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CS-W001157 4
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2-(2,5-Dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 942070-20-4

  • Cat. No. CS-0173882
  • Molecule weight238.15
  • Purity≥97%
  • MDL No.None

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

2-(2,5-Dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0173882

Structure of 942070-20-4

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General Information

  • CAS No. 942070-20-4
  • Cat. No. CS-0173882
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₉BO₂S
  • Molecular Weight 238.15
  • Synonym(s) 2,5-Dimethylthiophene-3-boronic acid pinacol ester
  • SMILES CC1=CC(B2OC(C)(C(C)(O2)C)C)=C(S1)C

Description

This boronate ester features a sterically hindered tetramethyl-1,3,2-dioxaborolane ring paired with a 2,5-dimethylthiophene moiety, delivering enhanced stability and reactivity in Suzuki-Miyaura coupling. The electron-rich thiophene unit facilitates efficient cross-coupling under mild conditions, enabling rapid access to complex arylated architectures in synthetic and medicinal chemistry workflows.

Application

2-(2,5-Dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The thiophene core imparts enhanced electronic stability and compatibility with diverse reaction conditions, enabling efficient C–C bond formation under mild catalytic systems. Its tetramethyl-substituted dioxaborolane ring ensures high chemical stability, resistance to hydrolysis, and ease of purification, making it ideal for modular synthesis of functionalized heterocycles and complex scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Harrisson, Peter; Morris, James; Marder, Todd B.; Steel, Patrick G. Organic Letters, 2009 , vol. 11, # 16 p. 3586 - 3589
  • Route2
    • In-stock
      2,5-Dimethylthiophene|CS-0022382
      638-02-8
    • null|null
      25015-63-8
    • ~99%
    • In-stock
      2-(2,5-Dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0173882
      942070-20-4

    References

    • Chotana, Ghayoor A.; Kallepalli, Venkata A.; Maleczka Jr., Robert E.; Smith III, Milton R. Tetrahedron, 2008 , vol. 64, # 26 p. 6103 - 6114

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.66414
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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