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CS-W001157 4
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Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

  • CAS No. 134892-19-6

  • Cat. No. CS-0173965
  • Purity≥98%
  • MDL No.MFCD10700151

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

Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate|CS-0173965

Structure of 134892-19-6

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General Information

  • CAS No. 134892-19-6
  • Cat. No. CS-0173965
  • Purity ≥98%
  • MDL No. MFCD10700151
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₅BO₄
  • Molecular Weight 256.15
  • Synonym(s) None
  • SMILES O=C(OC(C)(C)C)CCB1OC(C)(C)C(O1)(C)C

Description

Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate delivers a stable, bench-ready boronate ester for Suzuki-Miyaura cross-coupling. The tetramethyl-substituted dioxaborolane enhances shelf life and resistance to protodeboronation, while the tert-butyl ester facilitates orthogonal protection in complex synthesis. This reagent integrates seamlessly into late-stage functionalization workflows under mild conditions.

Application

Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The sterically protected boronate ester exhibits excellent functional group tolerance and facilitates efficient C–C bond formation under mild conditions. Its tert-butyl ester moiety enables straightforward conversion to the corresponding carboxylic acid or amide during late-stage diversification, making it a practical tool for constructing bioactive scaffolds in medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      540-88-5
    • In-stock
      2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0040849
      166330-03-6
    • ~91%
    • In-stock
      Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate|CS-0173965
      134892-19-6

    References

    • Hiscox, William C.; Matteson, Donald S. Journal of Organometallic Chemistry, 2000 , vol. 614-615, p. 314 - 317
  • Route2
    • null|null
      1663-39-4
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~92%
    • In-stock
      Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate|CS-0173965
      134892-19-6

    References

    • Elford, Tim G.; Nave, Stefan; Sonawane, Ravindra P.; Aggarwal, Varinder K. Journal of the American Chemical Society, 2011 , vol. 133, # 42 p. 16798 - 16801
  • Route3
    • null|null
      540-88-5
    • In-stock
      2-(Iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W005567
      70557-99-2
    • ~%
    • In-stock
      Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate|CS-0173965
      134892-19-6

    References

    • Tetrahedron Letters, , vol. 32, # 11 p. 1503 - 1506

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   44.76
  • LogP   2.8104
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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