5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

Base Information

• Chemical Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole
• CAS No.: 1086111-09-2
• Molecular Formula: C9H14BNO2S
• Molecular Weight: 211.093
• Hs Code.: 2934999090
• Mol file: 1086111-09-2.mol

Synonyms:5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole;Thiazole-5-boronic acid p...;Thiazol-5-ylboronic acid pinacol ester;2-dioxaborolan-2-yl)thiazole;5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3-thiazole;1,3-Thiazole-5-boronic acid, pinacol ester

Chemical Property of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

Chemical Property:

• Melting Point: 98 °C
• Boiling Point: 304.7±15.0 °C(Predicted)
• PKA: 2.57±0.10(Predicted)
• PSA: 59.59000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 1.44230
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

There total 7 articles about 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 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: 70.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-(trimethylsilyl)thiazole (79265-30-8) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3-thiazole (1086111-09-2)

Guidance literature:

2-(trimethylsilyl)thiazole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.583333h; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 2.75h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With acetic acid; In tetrahydrofuran; pH=5; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2009.05.013

Reference yield: 62.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Triisopropyl borate (5419-55-6) + 2-(trimethylsilyl)thiazole (79265-30-8) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3-thiazole (1086111-09-2)

Guidance literature:

2-(trimethylsilyl)thiazole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

Triisopropyl borate; In tetrahydrofuran; at -78 ℃; for 3h;

2,3-dimethyl-2,3-butane diol; Further stages;

DOI:10.1002/ejoc.202101397

Reference yield:

5-bromo-1,3-thiazole (3034-55-7) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3-thiazole (1086111-09-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 12h;

DOI:10.1021/acs.jmedchem.5b00464

upstream raw materials:

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

2-(trimethylsilyl)thiazole

5-bromo-1,3-thiazole

bis(pinacol)diborane

Downstream raw materials:

5-phenylthiazole

3-(thiazol-5-yl)benzaldehyde

5-(4-methoxyphenyl)thioazole

3-(thiazol-5-yl)benzonitrile

Refernces

• 1、 Hayes, Hannah L. D.,Wei, Ran,Assante, Michele,Geogheghan, Katherine J.,Jin, Na,Tomasi, Simone,Noonan, Gary,Leach, Andrew G.,Lloyd-Jones, Guy C.. "Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis". supporting information. p. 14814 - 14826. Retrieved 2021/09/13.
• 2、 Primas, Nicolas,Bouillon, Alexandre,Lancelot, Jean-Charles,El-Kashef, Hussein,Rault, Sylvain. "Synthesis of 5-arylthiazoles. Comparative study between Suzuki cross-coupling reaction and direct arylation". experimental part. p. 5739 - 5746. Retrieved 2009/12/03.