CAS 269410-08-4 Pyrazole-4-boronic acid pinacol ester

NAVIGATION

Pyrazole-4-boronic acid pinacol ester

PRICE INQUIRY

Catalog Number

ACM269410084

CAS Number

269410-08-4

Product Name

Pyrazole-4-boronic acid pinacol ester

Structure

Category

Salt

IUPAC Name

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Molecular Weight

194.04g/mol

Molecular Formula

C9H15BN2O2

Canonical SMILES

B1(OC(C(O1)(C)C)(C)C)C2=CNN=C2

InChI

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

Application

Pyrazole-4-boronic acid pinacol ester serves as a versatile reagent for various organic synthesis applications. Primarily, it is utilized in Suzuki-Miyaura cross-couplings and ruthenium-catalyzed asymmetric hydrogenation reactions. Moreover, it plays a crucial role in the development of inhibitors targeting a wide range of important therapeutic enzymes and kinases that incorporate the privileged pyrazole scaffold. These targets include VEGF, Aurora, Rho (ROCK), Janus Kinase 2 (JAK), c-MET, ALK, S-nitrosoglutathione reductase, CDC7, Acetyl-CoA carboxylase, the prosurvival Bcl-2 protein, viral RNA-dependent RNA polymerase, Long Chain Fatty Acid Elongase 6, PI3, AKT, Chk1, and Protein Kinase B. The compound is typically presented as an off-white to tan powder, highlighting its broad applicability in medicinal chemistry and drug discovery efforts.

Complexity

217

Covalently-Bonded Unit Count

Exact Mass

194.122658g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

194.122658g/mol

Rotatable Bond Count

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