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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

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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.
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