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525057 Sigma-Aldrich

4-Pyrazoleboronic acid pinacol ester

97%

Synonym: 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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Properties

Related Categories Boronate Esters, Boronic Acids and Derivatives, Chemical Synthesis, Heteroaryl Boronate Esters, Organometallic Reagents More...
Quality Level   100
assay   97%
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

Description

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

Packaging

1, 5, 25 g in glass bottle

Legal Information

Product of Boron Molecular

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Boronic Acid Esters - Chemfiles Volume 4 Article 2

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available. Several years ago, Miyaura et al. demonst...
Chemfiles Volume 4 Article 2
Keywords: Coupling reactions, Suzuki-Miyaura coupling

Peer-Reviewed Papers
15

References

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