Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate

Base Information

• Chemical Name: Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
• CAS No.: 741709-57-9
• Molecular Formula: C₁₄H₂₀BNO₄
• Molecular Weight: 277.128
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00433495
• Wikidata: Q82247656
• Mol file: 741709-57-9.mol

Synonyms:741709-57-9;ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate;Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-Pyridinecarboxylic acid ethyl ester;6-(Ethoxycarbonyl)pyridine-3-boronic acid pinacol ester;DTXSID00433495;Ethyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate;MFCD12923436;DS-7100;SB21524;C76370;EN300-23999259;J-521063;Z2044750681;ethyl 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)picolinate;ethyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate;Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarboxylate

Chemical Property of Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate

Chemical Property:

• Boiling Point: 397.1±27.0 °C(Predicted)
• PKA: 1.82±0.12(Predicted)
• PSA: 57.65000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 1.55750
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 277.1485383
• Heavy Atom Count: 20
• Complexity: 356

Purity/Quality:

97% ^*data from raw suppliers

Ethyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)C(=O)OCC

Technology Process of Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate

There total 6 articles about Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate 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: 77.0%

ethyl-2-picolinate (2524-52-9,1228273-66-2) + bis(pinacol)diborane (73183-34-3) → ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (741709-57-9)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 8-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-one; potassium tert-butylate; In tetrahydrofuran; at 80 ℃; for 12h; Reagent/catalyst; regioselective reaction; Glovebox; Sealed tube;

DOI:10.1021/jacs.7b04490

Reference yield: 75.0%

5-bromo-pyridine-2-carboxylic acid ethyl ester (77199-09-8) + bis(pinacol)diborane (73183-34-3) → ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (741709-57-9)

Guidance literature:

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

Reference yield: 70.0%

ethyl-2-picolinate (2524-52-9,1228273-66-2) + bis(pinacol)diborane (73183-34-3) → ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (741709-57-9) + ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine-2-carboxylate

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 1-(2-([2,2'-bipyridin]-5-yl)phenyl)-3-(4-trifluoromethylphenyl)urea; In para-xylene; at 25 ℃; for 18h; Overall yield = 70 %;

upstream raw materials:

ethyl-2-picolinate

bis(pinacol)diborane

5-bromo-pyridine-2-carboxylic acid ethyl ester

2,5-dibromopyridine

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