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CS-W001157 4
Total: USD 88.00

(1-Isopropyl-1H-pyrazol-5-yl)boronic acid

  • CAS No. 839714-33-9

  • Cat. No. CS-B1110
  • Purity≥95%
  • MDL No.MFCD11098002

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

(1-Isopropyl-1H-pyrazol-5-yl)boronic acid|CS-B1110

Structure of 839714-33-9

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General Information

  • CAS No. 839714-33-9
  • Cat. No. CS-B1110
  • Purity ≥95%
  • MDL No. MFCD11098002
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₁BN₂O₂
  • Molecular Weight 153.97
  • Synonym(s) B-[1-(1-methylethyl)-1H-pyrazol-5-yl]-Boronic acid
  • SMILES CC(N1N=CC=C1B(O)O)C

Description

This boronate moiety integrates a sterically hindered pyrazole scaffold, enhancing stability and solubility in polar solvents. The isopropyl group imparts favorable handling characteristics, enabling reliable use in Suzuki-Miyaura cross-coupling reactions under standard conditions.

Application

(1-Isopropyl-1H-pyrazol-5-yl)boronic acid serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. Its pyrazole core provides enhanced stability and solubility compared to simpler arylboronic acids, while the isopropyl substituent improves bench handling and reduces protodeboronation. The compound exhibits good functional group tolerance and facilitates the synthesis of substituted heterocycles relevant to medicinal chemistry and agrochemical development.

Synthesis

  • Route1

    References

    • Teegarden, Bradley R.; Li, Hongmei; Jayakumar, Honnappa; Strah-Pleynet, Sonja; Dosa, Peter I.; Selaya, Susan D.; Kato, Naomi; Elwell, Katie H.; Davidson, Jarrod; Cheng, Karen; Saldana, Hazel; Frazer, John M.; Whelan, Kevin; Foster, Jonathan; Espitia, Stephan; Webb, Robert R.; Beeley, Nigel R. A.; Thomsen, William; Morairty, Stephen R.; Kilduff, Thomas S.; Al-Shamma, Hussien A. Journal of Medicinal Chemistry, 2010 , vol. 53, # 5 p. 1923 - 1936
  • Route2

    References

    • Roche Palo Alto LLC Patent: US2009/170873 A1, 2009 ; Location in patent: Page/Page column 48 ;

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

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Computational Chemistry Data

  • TPSA   58.28
  • LogP   -0.8562
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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