methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate

Base Information

• Chemical Name: methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate
• CAS No.: 1381957-27-2
• Molecular Formula: C₂₀H₂₃BO₄
• Molecular Weight: 338.211
• Mol file: 1381957-27-2.mol

Synonyms:

Chemical Property of methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate

Chemical Property:

• Boiling Point: 458.0±38.0 °C(Predicted)
• Density: 1.12±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

Methyl4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate

There total 11 articles about methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate 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: 93.0%

4-methoxycarbonylphenyl bromide (619-42-1) + trimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)stannane → methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate (1381957-27-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃; for 12h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo402618r

Reference yield: 73.1%

methyl 4’-bromo-[1,1’-diphenyl]-4-carboxylate (89901-03-1) + bis(pinacol)diborane (73183-34-3) → methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate (1381957-27-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 48h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201406332

Reference yield: 48.0%

methyl 4-(4-tolyl)benzoate (49742-56-5) + bis(pinacol)diborane (73183-34-3) → methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate (1381957-27-2)

Guidance literature:

methyl 4-(4-tolyl)benzoate; With tert.-butylnitrite; N-hydroxyphthalimide; lithium bromide; In acetonitrile; at 80 ℃; for 24h; Inert atmosphere; Schlenk technique; Molecular sieve; Sealed tube;

bis(pinacol)diborane; With isonicotinate tert-butyl ester; at 110 ℃; for 15h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1002/anie.201901783

upstream raw materials:

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

bis(pinacol)diborane

4-methoxycarbonylphenyl bromide

1,4-phenylenediamine

Downstream raw materials:

(S)-methyl 4'-(6-(2-((4-cyanophenylethyl)carbamoyl)azetidin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)-[1,1'-biphenyl]-4-carboxylate

4-(4-{6-[(2S)-2-{[2-(4-cyanophenyl)ethyl]carbamoyl}azetidin-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl}phenyl)benzoic acid