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CS-W001157 4
Total: USD 88.00

4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane

  • CAS No. 476004-80-5

  • Cat. No. CS-0041968
  • Purity≥95%
  • MDL No.MFCD05664108

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

4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0041968

Structure of 476004-80-5

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General Information

  • CAS No. 476004-80-5
  • Cat. No. CS-0041968
  • Purity ≥95%
  • MDL No. MFCD05664108
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇BO₂S
  • Molecular Weight 224.13
  • Synonym(s) 5-(2-Methylthiophene)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane
  • SMILES CC1=CC=C(B2OC(C)(C)C(C)(C)O2)S1

Description

This boronate ester features a sterically protected dioxaborolane ring paired with a para-methylthiophene moiety, enabling robust coupling in Suzuki-Miyaura reactions. The tetramethyl substitution enhances stability and solubility under standard conditions, while the thiophene group facilitates efficient cross-coupling with aryl halides.

Application

4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane enhances air and moisture stability while maintaining high reactivity in palladium-catalyzed coupling with aryl and heteroaryl halides. Its methylthiophene moiety provides a versatile handle for constructing biologically relevant heterocyclic scaffolds, particularly in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • In-stock
      2-Methylthiophene|CS-W011331
      554-14-3
    • null|null
      25015-63-8
    • ~88%
    • In-stock
      4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0041968
      476004-80-5

    References

    • Robbins, Daniel W.; Hartwig, John F. Organic Letters, 2012 , vol. 14, # 16 p. 4266 - 4269
  • Route2
    • In-stock
      2-Methylthiophene|CS-W011331
      554-14-3
    • null|null
      61676-62-8
    • ~96%
    • In-stock
      4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane|CS-0041968
      476004-80-5

    References

    • Wakioka, Masayuki; Nakamura, Yuki; Hihara, Yoshihiro; Ozawa, Fumiyuki; Sakaki, Shigeyoshi Organometallics, 2013 , vol. 32, # 15 p. 4423 - 4430
  • Route3

    References

    • Robbins, Daniel W.; Hartwig, John F. Organic Letters, 2012 , vol. 14, # 16 p. 4266 - 4269

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.35572
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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