1-(2-Trimethylsilanylethoxymethyl)-1H-pyrazole-5-boronic acid pinacol ester

Base Information

• Chemical Name: 1-(2-Trimethylsilanylethoxymethyl)-1H-pyrazole-5-boronic acid pinacol ester
• CAS No.: 903550-12-9
• Molecular Formula: C15H29BN203Si
• Molecular Weight: 324.303
• Hs Code.: 2934999090
• Mol file: 903550-12-9.mol

Synonyms:1-(2-Trimethylsilanylethoxymethyl)-1H-pyrazole-5-boronic acid pinacol ester;1-(2-Trimethylsilylethoxy)methylpyrazole-5-boronic acid, pinacol ester;5-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(triMethylsilyl)ethoxy)Methyl)-1H-pyrazole

Chemical Property of 1-(2-Trimethylsilanylethoxymethyl)-1H-pyrazole-5-boronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 4.31E-06mmHg at 25°C
• Boiling Point: 395.1°C at 760 mmHg
• Flash Point: 192.7°C
• PSA: 45.51000
• Density: 1.01g/cm³
• LogP: 2.49460
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(2-Trimethylsilanylethoxymethyl)-1H-pyrazole-5-boronic acid pinacol ester

There total 3 articles about 1-(2-Trimethylsilanylethoxymethyl)-1H-pyrazole-5-boronic acid pinacol ester 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: 75.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-pyrazole (133560-57-3) → 5-(4,4,5,5-tetramethyl-[1,3 ,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole (903550-12-9)

Guidance literature:

1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-pyrazole; With n-butyllithium; In tetrahydrofuran; at -70 ℃;

With Triisopropyl borate; In tetrahydrofuran; at -70 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In tetrahydrofuran; at -70 ℃;

DOI:10.1016/j.tetlet.2006.04.125

Reference yield:

3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (844501-71-9,1086111-17-2) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 5-(4,4,5,5-tetramethyl-[1,3 ,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole (903550-12-9)

Guidance literature:

3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole; With sodium hydride; In tetrahydrofuran; at 0 - 15 ℃; for 0.5h;

(2-trimethylethylsilylethoxy)methyl chloride; In tetrahydrofuran; at 15 ℃; for 12h;

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 5-(4,4,5,5-tetramethyl-[1,3 ,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole (903550-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / sodium hydride / tetrahydrofuran / 20 °C

2.1: n-BuLi / tetrahydrofuran / -70 °C

2.2: triisopropylborate / tetrahydrofuran / -70 °C

2.3: 75 percent / AcOH / tetrahydrofuran / -70 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2006.04.125

upstream raw materials:

2,3-dimethyl-2,3-butane diol

1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-pyrazole

(2-trimethylethylsilylethoxy)methyl chloride

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

Downstream raw materials:

5-(2-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole

2-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-benzoic acid methyl ester

2-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-benzaldehyde

2-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-benzonitrile

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