N-BOC-isoindoline-4-boronic acid, pinacol ester

Base Information

• Chemical Name: N-BOC-isoindoline-4-boronic acid, pinacol ester
• CAS No.: 1035235-28-9
• Molecular Formula: C19H30BNO5
• Molecular Weight: 345.247
• Hs Code.: 2933998090
• Mol file: 1035235-28-9.mol

Synonyms:N-BOC-isoindoline-4-boronic acid, pinacol ester;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate

Chemical Property of N-BOC-isoindoline-4-boronic acid, pinacol ester

Chemical Property:

• Boiling Point: 453.4±45.0 °C(Predicted)
• PKA: -1.66±0.20(Predicted)
• PSA: 48.00000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 3.17440

Purity/Quality:

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

N-BOC-isoindoline-4-boronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-BOC-isoindoline-4-boronic acid, pinacol ester

Technology Process of N-BOC-isoindoline-4-boronic acid, pinacol ester

There total 3 articles about N-BOC-isoindoline-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: 97.0%

tert-butyl 4-bromo-2,3-dihydro-1H-isoindole-2-carboxylate (1035235-27-8) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylic acid tert-butyl ester (1035235-28-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 16h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylic acid tert-butyl ester (1035235-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

Reference yield:

4-bromo-2,3-dihydro-1H-isoindole hydrochloride (923590-95-8) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylic acid tert-butyl ester (1035235-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 12 h / 10 - 20 °C

2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; triethylamine; In tetrahydrofuran; 1,4-dioxane;

upstream raw materials:

tert-butyl 4-bromo-2,3-dihydro-1H-isoindole-2-carboxylate

bis(pinacol)diborane

di-tert-butyl dicarbonate

4-bromo-2,3-dihydro-1H-isoindole hydrochloride

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