2-{4-[3-(dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-{4-[3-(dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 627899-90-5
• Molecular Formula: C17H28BNO3
• Molecular Weight: 305.225
• Hs Code.: 2934999090
• Mol file: 627899-90-5.mol

Synonyms:2-{4-[3-(Dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;N,N-Dimethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propan-1-amine;

Chemical Property of 2-{4-[3-(dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 8.36E-07mmHg at 25°C
• Refractive Index: 1.502
• Boiling Point: 406.1 °C at 760 mmHg
• Flash Point: 199.4 °C
• PSA: 30.93000
• Density: 1.02 g/cm³
• LogP: 2.31630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

4-[3-(Dimethylamino)propoxy]benzeneboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-{4-[3-(dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 4 articles about 2-{4-[3-(dimethylamino)propoxy]phenyl}-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: 48.0%

3-Dimethylamino-1-propanol (3179-63-3) + p-bromophenylboronic acid pinacol ester (68716-49-4) → N,N-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-1-amine (627899-90-5)

Guidance literature:

With tetrabutylammomium bromide; Ni(dtbbpy)₃Cl₂; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 20 ℃; for 8h; chemoselective reaction; Inert atmosphere; Electrochemical reaction; Molecular sieve; Sealed tube;

DOI:10.1002/anie.202107820

Reference yield: 45.0%

3-(4-bromophenoxy)-N,N-dimethyl-propan-1-amine (76579-64-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → N,N-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-1-amine (627899-90-5)

Guidance literature:

3-(4-bromophenoxy)-N,N-dimethyl-propan-1-amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.16667h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.dyepig.2014.08.007

Reference yield: 42.4%

3-(4-bromophenoxy)-N,N-dimethyl-propan-1-amine (76579-64-1) + bis(pinacol)diborane (73183-34-3) → N,N-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-1-amine (627899-90-5)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 90 ℃; for 16h; Inert atmosphere;

upstream raw materials:

3-(4-bromophenoxy)-N,N-dimethyl-propan-1-amine

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

bis(pinacol)diborane

3-Dimethylamino-1-propanol

Downstream raw materials:

(S)-2-(4-aminophenyl)-8-((5-(((S)-2-(4-(3-(dimethylamino)propoxy)phenyl)-7-methoxy-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)pentyl)oxy)-7-methoxy-10-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11(10H,11aH)-dione

3-{-4-[3-fluoro-6-(pyrid-3-yl)-9H-pyrrolo[2,3-b:5,4-c']dipyrid-4-yl]phenoxy}-N,N-dimethylpropan-1-amine

N,N-dimethyl-3-{4-[6-(pyrid-3-yl)-9H-pyrrolo[2,3-b:5,4-c']dipyrid-3-yl]phenoxy}propan-1-amine

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