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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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1 G
$43.44
5 G
$39.45
25 G
$144.00

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

$43.44

List Price$54.50Save 20%
Web-Only Promotion
41 left in stockDetails
Request a Bulk Order

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[1]
  • Ruthenium-catalyzed asymmetric hydrogenation[2]

Reagent used in preparation of inhibitors of many highly significant therapeutic enzymes and kinases containing the privileged scaffold pyrazole, including
  • VEGF[3]
  • Aurora[3][4]
  • Rho (ROCK)[2]
  • Janus Kinase 2 (JAK)[5]
  • c-MET[6]
  • ALK[6]
  • S-nitrosoglutathione reductase[7]
  • CDC7[8]
  • Acetyl-CoA carboxylase[9]
  • Prosurvival Bcl-2 protein[10]
  • Viral RNA-Dependent RNA polymerase[11]
  • Long Chain Fatty Acid Elongase 6[12]
  • PI3[13]
  • AKT[14]
  • Chk1[15]
  • Protein Kinase B[16]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV4721
MKCV3914
MKCQ2654
MKCM6467
MKCL2019

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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
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)
J Jean Cui et al.
Journal of medicinal chemistry, 54(18), 6342-6363 (2011-08-05)
Because of the critical roles of aberrant signaling in cancer, both c-MET and ALK receptor tyrosine kinases are attractive oncology targets for therapeutic intervention. The cocrystal structure of 3 (PHA-665752), bound to c-MET kinase domain, revealed a novel ATP site
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.
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.
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