2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 929626-16-4
• Molecular Formula: C13H18BClO3
• Molecular Weight: 268.548
• Hs Code.: 2934999090
• Mol file: 929626-16-4.mol

Synonyms:MeOClC6H3B(pin);(3-chloro-5-methoxyphenyl)boronic acid pinacol ester;MeOC6H3ClB(pinacolato);

Chemical Property of 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• PSA: 27.69000
• LogP: 2.64780
• Storage Temp.: 2-8°C

Purity/Quality:

96.0%Min ^*data from raw suppliers

3-Chloro-5-methoxyphenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 6 articles about 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 97.0%

1-chloro-3-methoxy-benzene (2845-89-8) + bis(pinacol)diborane (73183-34-3) → 2-(3-chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (929626-16-4)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole; at 100 ℃; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.5b05252

Reference yield: 90.0%

methyl iodide (74-88-4) → 2-(3-chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (929626-16-4)

Guidance literature:

3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; With sodium hydride; In tetrahydrofuran; for 0.166667h;

methyl iodide; In tetrahydrofuran;

Reference yield: 83.0%

1-chloro-3-methoxy-benzene (2845-89-8) → 2-(3-chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (929626-16-4)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1007/s11164-012-0725-4

upstream raw materials:

1-chloro-3-methoxy-benzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

methyl iodide

Downstream raw materials:

1-chloro-3-fluoro-5-methoxybenzene

C₁₄H₁₂ClFO

C₁₅H₁₅ClO₂

C₁₅H₁₅ClO

Refernces

• 1、 Ding, Siyi,Wang, Linghua,Miao, Zongcheng,Li, Pengfei. "NNB-type tridentate boryl ligands enabling a highly active iridium catalyst for C–H borylation". . . Retrieved 2019/04/30.
• 2、 Kallepalli, Venkata A,Gore, Kristin A.,Shi, Feng,Sanchez, Luis,Chotana, Ghayoor A.,Miller, Susanne L.,Maleczka, Robert E.,Smith, Milton R.. "Harnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization". . p. 8341 - 8353. Retrieved 2015/09/02.