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Merck
CN

525057

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
NACRES:
NA.22
PubChem Substance ID:
24874465
UNSPSC Code:
12352103
MDL number:
MFCD03453063

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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)

SMILES string

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

InChI key

TVOJIBGZFYMWDT-UHFFFAOYSA-N

assay

97%

form

solid

mp

142-146 °C (lit.)

Quality Level

100

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

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV4721
MKCV3914
MKCQ2654
MKCM6467
MKCL2019

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Discovery of Novel Benzoxazinones as Potent and Orally Active Long Chain Fatty Acid Elongase 6 Inhibitors
Mizutani, T.; et al.
Journal of Medicinal Chemistry, 52, 7989-7300 (2009)
Benjamin Perry et al.
Bioorganic & medicinal chemistry letters, 18(19), 5299-5302 (2008-09-09)
Optimization of the cellular and pharmacological activity of a novel series of PI3 kinase inhibitors targeting multiple isoforms is described.
Jesus R Medina et al.
Bioorganic & medicinal chemistry letters, 20(8), 2552-2555 (2010-03-26)
Novel Aurora inhibitors were identified truncating clinical candidate GSK1070916. Many of these truncated compounds retained potent activity against Aurora B with good antiproliferative activity. Mechanistic studies suggested that these compounds, depending on the substitution pattern, may or may not exert
Gordon Saxty et al.
Journal of medicinal chemistry, 50(10), 2293-2296 (2007-04-25)
Using fragment-based screening techniques, 5-methyl-4-phenyl-1H-pyrazole (IC50 80 microM) was identified as a novel, low molecular weight inhibitor of protein kinase B (PKB). Herein we describe the rapid elaboration of highly potent and ligand efficient analogues using a fragment growing approach.
Robert M Garbaccio et al.
Bioorganic & medicinal chemistry letters, 17(22), 6280-6285 (2007-09-29)
From HTS lead 1, a novel benzoisoquinolinone class of ATP-competitive Chk1 inhibitors was devised and synthesized via a photochemical route. Using X-ray crystallography as a guide, potency was rapidly enhanced through the installation of a tethered basic amine designed to
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