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525057

Sigma-Aldrich

4-Pyrazoleboronic acid pinacol ester

97%

Synonym(s):

4,4,5,5-Tetramethyl-2-(1H-pyrazol-2-yl)-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-(pyrazol-4-yl)-1,3,2-dioxaborolane, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole, Pyrazol-4-ylboronic acid pinacol ester

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About This Item

Linear Formula:
(CH3)4C2O2BC3N2H3
CAS Number:
269410-08-4
Molecular Weight:
194.04
MDL number:
MFCD03453063
UNSPSC Code:
12352103
PubChem Substance ID:
24874465
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

mp

142-146 °C (lit.)

SMILES string

CC1(C)OB(OC1(C)C)c2cn[nH]c2

InChI

1S/C9H15BN2O2/c1-8(2)9(3,4)14-10(13-8)7-5-11-12-6-7/h5-6H,1-4H3,(H,11,12)

InChI key

TVOJIBGZFYMWDT-UHFFFAOYSA-N

Related Categories

Application

Reagent used for
  • Suzuki-Miyaura cross-couplings
  • Ruthenium-catalyzed asymmetric hydrogenation

Reagent used in preparation of inhibitors of many highly significant therapeutic enzymes and kinases containing the privileged scaffold pyrazole, including
  • VEGF
  • Aurora
  • Rho (ROCK)
  • Janus Kinase 2 (JAK)
  • c-MET
  • ALK
  • S-nitrosoglutathione reductase
  • CDC7
  • Acetyl-CoA carboxylase
  • Prosurvival Bcl-2 protein
  • Viral RNA-Dependent RNA polymerase
  • Long Chain Fatty Acid Elongase 6
  • PI3
  • AKT
  • Chk1
  • Protein Kinase B

Legal Information

Product of Boron Molecular

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Mika Lindvall et al.
ACS medicinal chemistry letters, 2(10), 720-723 (2011-10-13)
A ligand-based 3D pharmacophore model for serine/threonine kinase CDC7 inhibition was created and successfully applied in the discovery of novel 2-(heteroaryl)-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-ones. The pharmacophore model provided a hypothesis for lead generation missed by docking to a homology model. Medicinal chemistry exploration
Design and evaluation of 3,6-di(hetero)aryl imidazo[1,2-a]pyrazines as inhibitors of checkpoint and other kinases
Matthews, T. P.; et al.
Bioorganic & Medicinal Chemistry, 20, 4045-4049 (2010)
Asymmetric synthesis of potent chroman-based Rho kinase (ROCK-II) inhibitors
Chen, Y-T.; et al.
MedChemComm, 2, 73-75 (2011)
Michael L Curtin et al.
Bioorganic & medicinal chemistry letters, 22(9), 3208-3212 (2012-04-03)
In an effort to identify multi-targeted kinase inhibitors with a novel spectrum of kinase activity, a screen of Abbott proprietary KDR inhibitors against a broad panel of kinases was conducted and revealed a series of thienopyridine ureas with promising activity
Hassan M Shallal et al.
Bioorganic & medicinal chemistry letters, 21(5), 1325-1328 (2011-02-09)
Overexpression of prosurvival or underexpression of pro-death Bcl-2 family proteins can lead to cancer cell resistance to chemotherapy and radiation treatment. Inhibition of the prosurvival Bcl-2 family proteins has become a strategy for cancer therapy and inhibitors are currently being
View All Related Papers

Articles

Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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