3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Base Information

• Chemical Name: 3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 445264-60-8
• Molecular Formula: C12H18BNO3
• Molecular Weight: 235.091
• Hs Code.: 2934999090
• European Community (EC) Number: 834-020-3
• DSSTox Substance ID: DTXSID10397599
• Wikidata: Q72485749
• Mol file: 445264-60-8.mol

Synonyms:445264-60-8;3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-Methoxypyridine-5-boronic acid pinacol ester;5-Methoxy-3-pyridineboronic acid pinacol ester;3-Methoxy-5-pyridineboronic acid pinacol ester;3-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;5-Methoxypyridine-3-boronic acid, pinacol ester;MFCD03412068;(5-METHOXYPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;Pyridine, 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;3-methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine;5-Methoxypyridine-3-boronic acid pinacol ester;Pyridine,3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;3-METHOXY-5-(PINACOLBORANATO)PYRIDINE;SCHEMBL182869;METHOXYPYRIDINE-3-BORONIC ACID,PINACOL ESTER;(3-METHOXYPYRIDIN-5-YL)BORONIC ACID PINACOL ESTER;DTXSID10397599;HENXUFOAGXNWKH-UHFFFAOYSA-N;CS-D1055;AKOS005259555;AB14355;GS-6575;AC-33450;SY016491;Methoxypyridine-3-boronic acid,pinacolester;FT-0694771;M2994;A25324;A25362;EN300-318550;3-methoxy-5-pyridine boronic acid pinacol ester;J-512769;5-Methoxy-3-pyridineboronic acid pinacol ester, 97%;Z1336747321;3-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-pyridine;3-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)-pyridine;5-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;5-Methoxy-3-pyridineboronic Acid Pinacol Ester

Chemical Property of 3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property:

• Vapor Pressure: 0.000116mmHg at 25°C
• Melting Point: 100-108 °C
• Refractive Index: 1.489
• Boiling Point: 346.3 °C at 760 mmHg
• Flash Point: 163.3 °C
• PSA: 40.58000
• Density: 1.067 g/cm³
• LogP: 1.38940
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 235.1379736
• Heavy Atom Count: 17
• Complexity: 267

Purity/Quality:

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

3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CN=C2)OC
• Uses: 3-Methoxypyridine-5-boronic acid pinacol ester is for use in Suzuki-Miyaura aryl-aryl cross-coupling. 5-Methoxy-3-pyridineboronic acid pinacol ester can be used:To synthesize anthracene based bis-pyridine ligand (L), which is employed in the preparation of fluorescent M2L4 type capsules (M= Pt, Zn, Pd, Cu, Ni, Co, and Mn).As a starting material in the synthesis of pyridylmethyl?pyridine derivatives as potent 11β-hydroxylase (CPY11B1) inhibitors.

Technology Process of 3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

There total 5 articles about 3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 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: 95.0%

3-methoxypyridine (7295-76-3,1232006-42-6) + bis(pinacol)diborane (73183-34-3) → 3-methoxy-5-pyridineboronic acid pinacol ester (445264-60-8)

Guidance literature:

bis(pinacol)diborane; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₅₁H₃₂N₈Zn; In para-xylene; at 20 ℃; for 0.5h; Schlenk technique;

3-methoxypyridine; In para-xylene; at 80 ℃; for 24h; regioselective reaction; Schlenk technique;

DOI:10.1002/anie.202101997

Reference yield: 83.0%

3-bromo-5-methoxypyridine (50720-12-2) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 3-methoxy-5-pyridineboronic acid pinacol ester (445264-60-8)

Guidance literature:

3-bromo-5-methoxypyridine; With n-butyllithium; In diethyl ether; hexane; at -80 ℃; Inert atmosphere;

With Trimethyl borate; In diethyl ether; hexane; at -80 - 20 ℃; for 12h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether; hexane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c1cc12946e

Reference yield:

3-bromo-5-methoxypyridine (50720-12-2) + bis(pinacol)diborane (73183-34-3) → 3-methoxy-5-pyridineboronic acid pinacol ester (445264-60-8)

Guidance literature:

3-bromo-5-methoxypyridine; bis(pinacol)diborane; With potassium acetate; In 1,4-dioxane; for 0.25h;

With tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; at 80 ℃; for 16.25h;

upstream raw materials:

3-bromo-5-methoxypyridine

bis(pinacol)diborane

3,5-dibromopyridine

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

Refernces

• 1、 -. "Compound containing L-prolinamide fragment, and preparation method and application thereof". Paragraph 0112; 0113. . Retrieved 2017/07/12.
• 2、 -. "INHIBITORS OF THE KYNURENINE PATHWAY". Page/Page column 156. . Retrieved 2014/12/12.