2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester

Base Information

• Chemical Name: 2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester
• CAS No.: 957062-72-5
• Molecular Formula: C13H18BNO4
• Molecular Weight: 263.101
• Hs Code.: 2933399990
• European Community (EC) Number: 802-060-0
• DSSTox Substance ID: DTXSID00590557
• Wikidata: Q72489534
• Mol file: 957062-72-5.mol

Synonyms:2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester;2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester;Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate;

Chemical Property of 2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester

Chemical Property:

• Boiling Point: 391.1±27.0 °C(Predicted)
• PKA: 1.27±0.10(Predicted)
• PSA: 57.65000
• Density: 1.12
• LogP: 1.16740
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 263.1328882
• Heavy Atom Count: 19
• Complexity: 343

Purity/Quality:

98%min ^*data from raw suppliers

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarboxylicAcidMethylEster ^*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=CC(=NC=C2)C(=O)OC
• Uses: 2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester can be used as a reagent to synthesize phenylaminodiheteroarylpyrimidine derivatives and analogs for use as antibacterial agents. 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarboxylic Acid Methyl Ester can be used as a reagent to synthesize phenylaminodiheteroarylpyrimidine derivatives and analogs for use as antibacterial agents.

Technology Process of 2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester

There total 1 articles about 2-(Methoxycarbonyl)-4-pyridineboronic 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:

methyl 4-bromopyridine-2-carboxylate (29681-42-3) + bis(pinacol)diborane (73183-34-3) → methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (957062-72-5)

Guidance literature:

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

Reference yield: 65.0%

N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide (1083326-17-3) + methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (957062-72-5) → methyl 6-chloro-5-(phenylsulfonamido)-[3,4'-bipyridine]-2'-carboxylate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In 1,4-dioxane; at 80 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.ejmech.2019.112012

Reference yield: 60.0%

methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (957062-72-5) + C28H34BrN3O5 → C35H40N4O7

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; In 1,2-dimethoxyethane; at 120 ℃; for 0.75h; Sealed tube; Inert atmosphere; Microwave irradiation;

upstream raw materials:

methyl 4-bromopyridine-2-carboxylate

bis(pinacol)diborane

Downstream raw materials:

isopropyl 1-isopropyl-4-(4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)-1H-pyrrole-2-carboxylate

Refernces