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

Base Information

• Chemical Name: 1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• CAS No.: 761446-45-1
• Molecular Formula: C16H21BN2O2
• Molecular Weight: 284.166
• Hs Code.: 29331990
• European Community (EC) Number: 671-685-7
• DSSTox Substance ID: DTXSID80370495
• Nikkaji Number: J3.652.743I
• Wikidata: Q72442877
• Mol file: 761446-45-1.mol

Synonyms:761446-45-1;1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-(Phenylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester;1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;1-benzyl-4-1h-pyrazoleboronic acid, pinacol ester;1-Benzylpyrazole-4-boronic acid pinacol ester;1-BENZYL-4-PYRAZOLEBORONIC ACID PINACOL ESTER;MFCD03789252;1-Benzylpyrazole-4-boronic acid, pinacol ester;1-benzyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;SCHEMBL98814;1-benzyl-1h-pyrazole-4-boronic acid, pinacol ester;DTXSID80370495;ZVPORPUUZXIPEF-UHFFFAOYSA-N;(1-BENZYL-1H-PYRAZOL-4-YL)BORONIC ACID PINACOL ESTER;BCP22348;AKOS015950592;AB16116;AC-9173;AS-3002;BCP9000045;CS-W010030;AM804330;SY006076;BCP0726000025;B4364;FT-0644869;J3.652.743I;A22872;EN300-212555;1-Benzylpyrazole-4-boronic acid pinacol ester, 95%;A1-24356;J-504257;F2147-7153;Z1741960567;1-benzyl-4-(4,4,5,5-tetra methyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole;2-(1-Benzyl-1H-pyrazole-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1-Benzyl-4-pyrazolyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 1-Benzyl-4-pyrazole boronic acid pinacol ester

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

Chemical Property:

• Appearance/Colour: off-white to light yellow crystal
• Vapor Pressure: 3.93E-07mmHg at 25°C
• Melting Point: 86-90 °C(lit.)
• Refractive Index: 1.542
• Boiling Point: 427.932 °C at 760 mmHg
• PKA: 1.85±0.10(Predicted)
• Flash Point: 212.606 °C
• PSA: 36.28000
• Density: 1.071 g/cm³
• LogP: 2.23060
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Water Solubility.: Insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 284.1696081
• Heavy Atom Count: 21
• Complexity: 353

Purity/Quality:

98% ^*data from raw suppliers

1-Benzylpyrazole-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-23-22
• Safety Statements: 22-24/25-37/39-26-36/37/38

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)CC3=CC=CC=C3
• Uses: 1-Benzylpyrazole-4-boronic acid pinacol ester can be used:As a model compound in the study of the stability of boronate esters in different alcohols using the LCMS technique.As a substrate in the study of palladium-catalyzed methylation of heteroaryl boronate esters using iodomethane.As a substrate in the preparation of bromodifluoromethylthiolated arenes, applicable in the radiosynthesis of [18F]ArylSCF3 compounds.

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

There total 7 articles about 1-Benzyl-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: 79.0%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + benzyl bromide (100-39-0) → 1-(phenylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-45-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield: 74.0%

1-benzyl-4-bromo-1H-pyrazole (50877-41-3) + bis(pinacol)diborane (73183-34-3) → 1-(phenylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-45-1)

Guidance literature:

With C₅₄H₄₄NO₂PPdS; potassium acetate; In 2-methyltetrahydrofuran; at 90 ℃; for 24h; Reagent/catalyst; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b02414

Reference yield: 62.0%

1-benzyl-4-iodo-1H-pyrazole (50877-42-4) + bis(pinacol)diborane (73183-34-3) → 1-(phenylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-45-1)

Guidance literature:

With potassium acetate; 1,1'-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride-chloroform adduct; In N,N-dimethyl-formamide; at 85 ℃;

upstream raw materials:

1-benzyl-4-iodo-1H-pyrazole

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

benzyl bromide

bis(pinacol)diborane

Downstream raw materials:

7-(1-benzyl-1H-pyrazol-4-yl)-2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine

1,1-dimethylethyl (3R)-3-[({7-[1-(phenylmethyl)-1H-pyrazol-4-yl]pyrido[3,4-b]pyrazin-5-yl}amino)methyl]-1-piperidinecarboxylate

1-benzyl-4-methoxy-1H-pyrazole

C₂₁H₂₀ClN₅