2-(3-CHLORO-4-METHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

Base Information

• Chemical Name: 2-(3-CHLORO-4-METHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• CAS No.: 445303-10-6
• Molecular Formula: C13H18BClO2
• Molecular Weight: 252.549
• Hs Code.: 2934999090
• Mol file: 445303-10-6.mol

Synonyms:3-Chloro-4-methylphenylboronic acid pinacol ester

Chemical Property of 2-(3-CHLORO-4-METHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

Chemical Property:

• PSA: 18.46000
• LogP: 2.94760
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3-Chloro-4-methylphenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(3-CHLORO-4-METHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

There total 13 articles about 2-(3-CHLORO-4-METHYLPHENYL)-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: 92.0%

2-methylchlorobenzene (95-49-8) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(3-chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (445303-10-6)

Guidance literature:

(η4-1,5-cyclooctadiene)bis(1,3-dicyclohexylimidazolin-2-ylidene)iridium(I) trifluoroacetate; In further solvent(s); byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.0 mol% of Ir(COD)(1,3-dicyclohexylimidazolin-2-ylidene)2(CF3CO2) in 2-chlorotoluene; stirring and heating at 40°C for 10 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;

DOI:10.1016/j.jorganchem.2006.08.099

Reference yield: 82.0%

4-bromo-2-chlorotoluene (89794-02-5) + bis(pinacol)diborane (73183-34-3) → 2-(3-chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (445303-10-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 5h; Inert atmosphere;

Reference yield: 75.0%

1,3-dioxoisoindolin-2-yl 3-chloro-4-methylbenzoate + bis(pinacol)diborane (73183-34-3) → 2-(3-chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (445303-10-6)

Guidance literature:

With isonicotinate tert-butyl ester; at 110 ℃; for 15h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01950

upstream raw materials:

2-methylchlorobenzene

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

3-chloro-4-methyliodobenzene

4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane

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