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

Base Information

• Chemical Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• CAS No.: 269410-08-4
• Molecular Formula: C9H15BN2O2
• Molecular Weight: 194.041
• Hs Code.: 29331990
• European Community (EC) Number: 629-131-7
• DSSTox Substance ID: DTXSID40378836
• Nikkaji Number: J3.254.828H
• Wikidata: Q72503423
• Mol file: 269410-08-4.mol

Synonyms:269410-08-4;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;Pyrazole-4-boronic acid pinacol ester;4-Pyrazoleboronic acid pinacol ester;1h-pyrazole-4-boronic acid pinacol ester;pyrazole-4-boronic acid, pinacol ester;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;MFCD03453063;1h-pyrazole-4-boronic acid, pinacol ester;4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane;1H-Pyrazole, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;SCHEMBL98961;(1H-PYRAZOL-4-YL)BORONIC ACID PINACOL ESTER;DTXSID40378836;TVOJIBGZFYMWDT-UHFFFAOYSA-N;BCP02712;CS-D1164;BBL101319;STL555115;4-pyrazole boronic acid pinacol ester;4-pyrazolyl boronic acid pinacol ester;AKOS005258370;AB15498;AS-2979;SB11372;AC-22285;BP-12124;SY004218;4-Pyrazoleboronic acid pinacol ester, 97%;AM20090332;FT-0644221;T2756;EN300-92082;A22310;A818724;J-016620;J-513432;Z1255391278;2-(4-Pyrazolyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-pyrazole;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan2-yl)-1H-pyrazole;4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)[1,3,2]dioxaborolane;4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole;4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl)-1H-pyrazole;4-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-1H-pyrazole;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) 1H-pyrazole;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-H-pyrazole;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazole;4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

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

Chemical Property:

• Appearance/Colour: Off-white to tan powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 142-146 °C(lit.)
• Refractive Index: 1.487
• Boiling Point: 335.373 °C at 760 mmHg
• PKA: 13.36±0.50(Predicted)
• Flash Point: 156.628 °C
• PSA: 47.14000
• Density: 1.091 g/cm³
• LogP: 0.70890
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: DMSO, Ethyl Acetate, Methanol
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 194.1226579
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

4-Pyrazoleboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, F
• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CNN=C2
• Uses: 4-Pyrazoleboronic Acid Pinacol Ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds. 1H-Pyrazole-4-boronic acid pinacol ester is a useful reagent for Suzuki-Miyaura cross-couplings as well as Ruthenium-catalyzed asymmetric hydrogenation. It is also used as reagent for preparing VEGF, Aurora, RHO (ROCK), Janus Kinase 2, c-MET, ALK, S-nitrsoflutathione reductase, CDC7, Acetyl-CoA carboxylase inhibitors as well as other biologically active compounds. Reagent used forSuzuki-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, includingVEGF AuroraRho (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 6PI3 AKT Chk1 Protein Kinase B

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

There total 13 articles about 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

4-bromo-1H-pyrazole (2075-45-8) + bis(pinacol)diborane (73183-34-3) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate; In 1,4-dioxane; for 12h; Inert atmosphere; Reflux;

Reference yield: 94.0%

1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (1029716-44-6) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Guidance literature:

With hydrogenchloride; 2,3-dimethyl-2,3-butane diol; In water; at 10 - 25 ℃; for 4.083h;

Reference yield: 88.0%

NH-pyrazole (288-13-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; In tetrahydrofuran; at 80 ℃; for 4h; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201306511

upstream raw materials:

4-iodopyrazole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

AT7867

2-(4-chloro-phenyl)-2-[4-(1H-pyrazol-4-yl)-phenyl]-ethylamine

3-(3,4-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-phenyl]-propionic acid

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

Refernces

• 1、 -. "N-(1H-IMIDAZOL-2-YL)BENZAMIDE COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME AS ACTIVE INGREDIENT". Page/Page column 35. . Retrieved 2021/04/10.
• 2、 -. "Synthesis method of pyrazole-4-pinacolato diboron". Paragraph 0026-0029. . Retrieved 2020/02/14.