{[5-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine

Base Information

• Chemical Name: {[5-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine
• CAS No.: 1384216-47-0
• Molecular Formula: C15H23BClNO2
• Molecular Weight: 295.617
• Hs Code.: 2931900090
• Mol file: 1384216-47-0.mol

Synonyms:{[5-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine;4-Chloro-2-(N,N-dimethylaminomethyl)phenylboronic acid, pinacol ester

Chemical Property of {[5-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine

Chemical Property:

• Boiling Point: 361.7±37.0 °C(Predicted)
• PKA: 8.55±0.28(Predicted)
• PSA: 21.70000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 2.70080

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloro-2-(N,N-dimethylaminomethyl)phenylboronicacid,pinacolester ^*data from reagent suppliers

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Technology Process of {[5-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine

There total 2 articles about {[5-chloro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine 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: 55.0%

1-(3-chlorophenyl)-N,N-dimethylmethanamine (15184-97-1) + bis(pinacol)diborane (73183-34-3) → C15H23BClNO2 (1384216-50-5) + 1-[5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N,N-dimethylmethanamine (1384216-47-0) + C21H34B2ClNO4

Guidance literature:

With 2-(Aminomethyl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In methyl cyclohexane; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol301635x

Reference yield:

1-bromomethyl-3-chlorobenzene (766-80-3) → C15H23BClNO2 (1384216-50-5) + 1-[5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N,N-dimethylmethanamine (1384216-47-0) + C21H34B2ClNO4

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol; water / 4 h / Inert atmosphere; Reflux

2: 2-(Aminomethyl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / methyl cyclohexane / 16 h / 70 °C / Inert atmosphere

With 2-(Aminomethyl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In ethanol; water; methyl cyclohexane;

DOI:10.1021/ol301635x

Reference yield: 48.0%

1-[5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N,N-dimethylmethanamine (1384216-47-0) + aniline (62-53-3) → 4-chloro-2-((dimethylamino)methyl)-N-phenylaniline + 1,1'-(4,4'-dichloro-[1,1'-biphenyl]-2,2'-diyl)bis(N,N-dimethylmethanamine)

Guidance literature:

With oxygen; copper(II) acetate monohydrate; In acetonitrile; at 80 ℃; for 2h; chemoselective reaction; Schlenk technique; Molecular sieve;

DOI:10.1021/acs.joc.5b01074

upstream raw materials:

1-(3-chlorophenyl)-N,N-dimethylmethanamine

bis(pinacol)diborane

1-bromomethyl-3-chlorobenzene

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