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CS-W001157 4
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(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acid

  • CAS No. 109299-79-8

  • Cat. No. CS-0001971
  • Purity≥98%
  • MDL No.MFCD01318980

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

(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acid|CS-0001971

Structure of 109299-79-8

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General Information

  • CAS No. 109299-79-8
  • Cat. No. CS-0001971
  • Purity ≥98%
  • MDL No. MFCD01318980
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₁BN₂O₄
  • Molecular Weight 268.12
  • Synonym(s) [2,4-bis(tert-butoxy)pyriMidin-5-yl]boronic acid
  • SMILES OB(C1=CN=C(OC(C)(C)C)N=C1OC(C)(C)C)O

Description

This boronate moiety integrates a sterically shielded pyrimidine core, enabling robust coupling in Suzuki-Miyaura reactions. The 2,4-di-tert-butoxy substitution pattern enhances solubility and stability under standard conditions, while the para-boronate functionality facilitates efficient C–C bond formation with aryl halides.

Application

(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acid serves as a stable, bench-friendly building block for constructing pyrimidine-based scaffolds via Suzuki-Miyaura coupling. Its ortho-di-tert-butyl substitution enhances solubility and minimizes protodeboronation, enabling reliable cross-coupling with aryl and heteroaryl halides under standard conditions. The boronic acid functionality exhibits high functional group tolerance and facilitates the synthesis of complex heterocyclic architectures relevant to medicinal chemistry and agrochemical development.

Synthesis

  • Route1

    References

    • Journal of Fluorine Chemistry, , vol. 135, p. 225 - 230

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   84.7
  • LogP   0.511
  • H_Acceptors   6
  • H_Donors   2
  • Rotatable_Bonds   3

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