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CS-W001157 4
Total: USD 88.00

2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 82954-89-0

  • Cat. No. CS-W000975
  • Purity≥98%
  • MDL No.MFCD19441153

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

2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W000975

Structure of 82954-89-0

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General Information

  • CAS No. 82954-89-0
  • Cat. No. CS-W000975
  • Purity ≥98%
  • MDL No. MFCD19441153
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₇BO₂
  • Molecular Weight 156.03
  • Synonym(s) Ethylboronic Acid Pinacol Ester
  • SMILES CCB1OC(C(O1)(C)C)(C)C

Description

2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane offers a stable, bench-ready boronate handle ideal for Suzuki-Miyaura cross-coupling reactions. The sterically shielded dioxaborolane ring enhances shelf life and resistance to hydrolysis, while the ethyl substituent improves solubility in organic media. This reagent enables efficient coupling under mild conditions with minimal byproduct formation.

Application

2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron source for Suzuki-Miyaura cross-coupling reactions. Its sterically protected dioxaborolane ring enhances air and moisture stability while enabling efficient coupling with aryl, vinyl, and heteroaryl halides under mild conditions. The ethyl substituent provides improved solubility and reactivity balance, facilitating purification and integration into multi-step syntheses of complex molecules.

Synthesis

  • Route1

    References

    • Stymiest, Jake L.; Dutheuil, Guillaume; Mahmood, Adeem; Aggarwal, Varinder K. Angewandte Chemie - International Edition, 2007 , vol. 46, # 39 p. 7491 - 7494
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      2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W000975
      82954-89-0
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      75927-49-0

    References

    • Montiel-Palma, Virginia; Lumbierres, Maria; Donnadieu, Bruno; Sabo-Etienne, Slyviane; Chaudret, Bruno Journal of the American Chemical Society, 2002 , vol. 124, # 20 p. 5624 - 5625
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    • In-stock
      2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W000975
      82954-89-0

    References

    • Fandrick, Daniel R.; Fandrick, Keith R.; Reeves, Jonathan T.; Tan, Zhulin; Johnson, Courtney S.; Lee, Heewon; Song, Jinhua J.; Yee, Nathan K.; Senanayake, Chris H. Organic Letters, 2010 , vol. 12, # 1 p. 88 - 91

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS07
Signal Word : Danger
UN#: 3272
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226-H315-H319
Precautionary Statements : P210-P233-P240-P241-P242-P243-P264-P280-P302+P352-P362-P370+P378-P501

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.0985
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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