2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 321574-04-3
• Molecular Formula: C₁₃H₁₈BBrO₂
• Molecular Weight: 297
• Mol file: 321574-04-3.mol

Synonyms:

Chemical Property of 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Boiling Point: 343.8±35.0 °C(Predicted)
• Density: 1.26±0.1 g/cm3(Predicted)

Purity/Quality:

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

2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 5 articles about 2-(4-bromo-2-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: 64.0%

2-methyl-4-bromoiodobenzene (116632-39-4) + bis(pinacol)diborane (73183-34-3) → 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (321574-04-3)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium acetate; In 1,4-dioxane; for 24h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c00178

Reference yield: 54.0%

2-methyl-4-bromoiodobenzene (116632-39-4) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (321574-04-3)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; toluene; at 80 ℃; for 6h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.6b11757

Reference yield: 54.0%

→ 2-(4-bromo-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (321574-04-3)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; toluene; at 80 ℃; for 6h; Sealed tube;

upstream raw materials:

bis(pinacol)diborane

2-methyl-4-bromoiodobenzene

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

Refernces

• 1、 -. "METHODS OF MANUFACTURING OF BORON COMPOUND WITHOUT TRANSITION METALS". Paragraph 0062; 0063; 0071; 0072; 0076. . Retrieved 2018/05/03.
• 2、 Willis,Strongin. "Palladium-catalyzed borylation of aryldiazonium tetrafluoroborate salts. A new synthesis of arylboronic esters". . p. 8683 - 8686. Retrieved 2007/10/03.