ethyl 5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate

Base Information

• Chemical Name: ethyl 5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate
• CAS No.: 960116-27-2
• Molecular Formula: C₁₃H₁₉BO₄S
• Molecular Weight: 282.168
• Mol file: 960116-27-2.mol

Synonyms:ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate

Chemical Property of ethyl 5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate

Chemical Property:

• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

97% ^*data from raw suppliers

5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-3-carboxylic acid ethyl ester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of ethyl 5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate

There total 2 articles about ethyl 5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate 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:

5-bromo-3-thiophenecarboxylic acid ethyl ester (170355-38-1) + bis(pinacol)diborane (73183-34-3) → ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate (960116-27-2)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80 ℃;

Reference yield:

thiophene-3-carboxylic acid ethyl ester (5751-80-4) + bis(pinacol)diborane (73183-34-3) → ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate (960116-27-2)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; Inert atmosphere; Glovebox;

thiophene-3-carboxylic acid ethyl ester; In tetrahydrofuran; at 65 ℃; for 24h; regioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.201916015

Reference yield: 42.0%

6-chloropyridin-2-amine (45644-21-1) + ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate (960116-27-2) → ethyl 5-(6-aminopyridin-2-yl)thiophene-3-carboxylate

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 80 ℃; for 18h; Inert atmosphere;

upstream raw materials:

5-bromo-3-thiophenecarboxylic acid ethyl ester

bis(pinacol)diborane

thiophene-3-carboxylic acid ethyl ester

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