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

• ChemBase ID: 67368
• Molecular Formular: C9H15BN2O2
• Molecular Mass: 194.0386
• Monoisotopic Mass: 194.12265813
• SMILES: [nH]1ncc(c1)B1OC(C(O1)(C)C)(C)C
• Canonical SMILES: CC1(C)OB(OC1(C)C)c1c[nH]nc1
• 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)
• InChIKey: TVOJIBGZFYMWDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• IUPAC Traditional name: 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• Synonyms: 4,4,5,5-Tetramethyl-2-(1H-pyrazol-2-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; 4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane; 4-Pyrazoleboronic acid pinacol ester; 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole; 1H-Pyrazole-4-boronic acid, pinacol ester; 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE; 1H-Pyrazole-4-boronic acid pinacol ester; (1H-Pyrazol-4-yl)boronic acid pinacol ester; 1H-Pyrazole-4-boronic Acid Pinacol Ester; 2-(1H-Pyrazol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4-Pyrazoleboronic acid pinacol ester; 4,4,5,5-四甲基-2-(1H-吡唑-4-基)-1,3,2-二氧杂戊硼烷; 4-吡唑硼酸频哪醇酯; 1H-吡唑-4-硼酸频哪醇酯

Database IDs

• CAS Number: 269410-08-4
• MDL Number: MFCD03453063
• PubChem SID: 162033103; 24874465
• PubChem CID: 2774010

CALCULATED PROPERTIES

• Acid pKa: 9.617226
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.2277198
• LogD (pH = 7.4): 2.2251956
• Log P: 2.2278
• Molar Refractivity: 49.4005 cm^3
• Polarizability: 20.819656 Å^3
• Polar Surface Area: 47.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 142-146 °C(lit.); 142-146°C; 145-149°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 97%; 98%
• Linear Formula: (CH3)4C2O2BC3N2H3

DETAILS

Sigma Aldrich - 525057

Packaging
1, 5, 25 g in glass bottle
Legal Information
Product of Boron Molecular
Application
Reagent used for
• Suzuki-Miyaura cross-couplings1
• Ruthenium-catalyzed asymmetric hydrogenation2 Reagent used in preparation of inhibitors of many highly significant therapeutic enzymes and kinases containing the privileged scaffold pyrazole, including
• VEGF3
• Aurora3,4
• Rho (ROCK)2
• Janus Kinase 2 (JAK)5
• c-MET6
• ALK6
• S-nitrosoglutathione reductase7
• CDC78
• Acetyl-CoA carboxylase9
• Prosurvival Bcl-2 protein10
• Viral RNA-Dependent RNA polymerase11
• Long Chain Fatty Acid Elongase 612
• PI313
• AKT14
• Chk115
• Protein Kinase B16

Toronto Research Chemicals - P842200

4-Pyrazoleboronic Acid Pinacol Ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

REFERENCES

• Chowdhury, S. et al.: Bioorg. Med. Chem. Lett., 21, 7107 (2011)