1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLINE

Base Information

• Chemical Name: 1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLINE
• CAS No.: 934570-43-1
• Molecular Formula: C₁₅H₂₂BNO₂
• Molecular Weight: 259.156
• Mol file: 934570-43-1.mol

Synonyms:1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLINE

Chemical Property of 1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLINE

Chemical Property:

• PSA: 21.70000
• LogP: 2.04310

Purity/Quality:

98% ^*data from raw suppliers

1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLINE

There total 2 articles about 1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLINE 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: 56.5%

5-bromo-1-methyl-2,3-dihydroindole (99848-78-9) + bis(pinacol)diborane (73183-34-3) → 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline (934570-43-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere; Sealed tube;

Reference yield: 32.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + C15H14BNO2 → 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline (934570-43-1)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 1h; Schlenk technique;

DOI:10.1002/anie.201611536

Reference yield: 80.0%

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline (934570-43-1) → 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (837392-62-8)

Guidance literature:

With N,N'-bis(salicylidene)-1,2-phenylene diaminocobalt(II); [Ru(1,10-phenanthroline-5,6-dione)₃](PF₆)₂; oxygen; In methanol; at 65 ℃; for 6h; under 760.051 Torr; Reagent/catalyst; Temperature; Solvent; Catalytic behavior;

DOI:10.1021/acs.orglett.9b00111

upstream raw materials:

2,3-dimethyl-2,3-butane diol

5-bromo-1-methyl-2,3-dihydroindole

bis(pinacol)diborane

Downstream raw materials:

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Refernces

• 1、 Yin, Qin,Klare, Hendrik F. T.,Oestreich, Martin. "Catalytic Friedel–Crafts C?H Borylation of Electron-Rich Arenes: Dramatic Rate Acceleration by Added Alkenes". supporting information. p. 3712 - 3717. Retrieved 2017/03/21.