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

Base Information

• Chemical Name: 4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 1171891-31-8
• Molecular Formula: C
• Molecular Weight: 219.091
• Hs Code.: 2934999090
• Mol file: 1171891-31-8.mol

Synonyms:4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Melting Point: 103-107 °C
• Boiling Point: 324.9±30.0 °C(Predicted)
• PKA: 5.89±0.20(Predicted)
• PSA: 31.35000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 1.68920
• Storage Temp.: -20°C

Purity/Quality:

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

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 4 articles about 4-Methyl-3-(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:

bis(pinacol)diborane (73183-34-3) + 3-Bromo-4-methylpyridin (3430-22-6) → 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1171891-31-8)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 120 ℃; for 1h; Microwave irradiation;

Reference yield:

picoline (108-89-4) + bis(pinacol)diborane (73183-34-3) → 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1171891-31-8)

Guidance literature:

With C₄₄H₇₂B₃IrN₂O₆; In tetrahydrofuran; at 80 ℃; for 7h; Inert atmosphere; Glovebox;

DOI:10.1021/ja412563e

Reference yield:

picoline (108-89-4) + bis(pinacol)diborane (73183-34-3) → 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1171891-31-8) + 4-methyl-3,5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3-(2-(2-(dicyclohexylboraneyl)ethyl)phenyl)-1,10-phenanthroline; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In 1,4-dioxane; at 25 ℃; for 0.166667h; Inert atmosphere; Glovebox;

picoline; In hexane; at 25 ℃; for 18h; Overall yield = 35 %; Overall yield = 100.8 mg; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/jacs.9b03138

upstream raw materials:

bis(pinacol)diborane

3-Bromo-4-methylpyridin

picoline

Downstream raw materials:

3-(4-methyl-3-pyridinyl)phenyl-2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

Refernces

• 1、 Larsen, Matthew A.,Hartwig, John F.. "Iridium-catalyzed C-H borylation of heteroarenes: Scope, regioselectivity, application to late-stage functionalization, and mechanism". supporting information. p. 4287 - 4299. Retrieved 2014/04/03.
• 2、 -. "Pyrrolopyrimidines and Pyrrolopyridines". Page/Page column 50-52. . Retrieved 2009/07/25.