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1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

  • CAS No. 1036991-40-8

  • Cat. No. CS-W000784
  • Purity≥97%
  • MDL No.MFCD09864189

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

1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W000784

Structure of 1036991-40-8

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General Information

  • CAS No. 1036991-40-8
  • Cat. No. CS-W000784
  • Purity ≥97%
  • MDL No. MFCD09864189
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉BN₂O₂
  • Molecular Weight 222.09
  • Synonym(s) 2-(1,5-Dimethyl-1H-pyrazol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • SMILES Cc1c(cnn1C)B1OC(C)(C)C(C)(C)O1

Description

1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole features a boronate ester group flanked by methyl-substituted pyrazole rings, delivering enhanced stability and reactivity in Suzuki-Miyaura coupling. This bench-stable reagent integrates seamlessly into C–C bond formation workflows, enabling efficient access to functionalized heterocycles under standard conditions.

Application

1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyrazole core provides orthogonal reactivity and metabolic stability, while the tetramethyl-substituted dioxaborolane enhances air and moisture tolerance. It facilitates efficient C–C bond formation with aryl and heteroaryl halides, enabling rapid access to functionalized heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • WO2010/51373 A1, ; Page/Page column 74 ; WO 2010/051373 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

  • TPSA   36.28
  • LogP   1.02772
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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