2,3-DIHYDRO-1H-ISOINDOL-1-ONE-4-BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2,3-DIHYDRO-1H-ISOINDOL-1-ONE-4-BORONIC ACID PINACOL ESTER
• CAS No.: 765948-78-5
• Molecular Formula: C14H18BNO3
• Molecular Weight: 259.113
• Hs Code.: 2931900090
• Mol file: 765948-78-5.mol

Synonyms:4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-2,3-dihydroisoindol-1-one;

Chemical Property of 2,3-DIHYDRO-1H-ISOINDOL-1-ONE-4-BORONIC ACID PINACOL ESTER

Chemical Property:

• Melting Point: 189-191 °C(Solv: hexane (110-54-3))
• Boiling Point: 483.191 °C at 760 mmHg
• PKA: 13.82±0.20(Predicted)
• Flash Point: 246.025 °C
• PSA: 47.56000
• Density: 1.163 g/cm³
• LogP: 1.55800
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

1H-Isoindol-1-one,2,3-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3-DIHYDRO-1H-ISOINDOL-1-ONE-4-BORONIC ACID PINACOL ESTER

There total 6 articles about 2,3-DIHYDRO-1H-ISOINDOL-1-ONE-4-BORONIC ACID PINACOL ESTER 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: 65.0%

→ 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (765948-78-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl acetamide; at 100 ℃; for 2h; Inert atmosphere;

Reference yield: 63.0%

bis(pinacol)diborane (73183-34-3) + 4-bromo-2,3-dihydro-isoindol-1-one (337536-15-9) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (765948-78-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1016/j.bmcl.2004.06.041

Reference yield:

methyl 3-bromo-2-methylbenzoate (99548-54-6) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (765948-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NBS; Bz₂O₂ / benzene

2: 87 percent / aq. NH₃ / tetrahydrofuran

3: 63 percent / PdCl₂(dppf); KOAc / dimethylformamide / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium hydroxide; N-Bromosuccinimide; potassium acetate; dibenzoyl peroxide; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.bmcl.2004.06.041

upstream raw materials:

bis(pinacol)diborane

4-bromo-2,3-dihydro-isoindol-1-one

methyl 3-bromo-2-methylbenzoate

3-bromo-2-methylbenzoic acid chloride

Downstream raw materials:

4-(4-amino-2-chlorophenyl)-1-isoindolinone

4-(4-amino-3,5-dimethyl-phenyl)-2,3-dihydro-isoindol-1-one

4-(4-amino-3-fluorophenyl)-1-isoindolinone

4-[4-amino-3-(trifluoromethyl)phenyl]-1-isoindolinone

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