Benzenemethanamine, 2-ethenyl-N-methyl-

Base Information

• Chemical Name: Benzenemethanamine, 2-ethenyl-N-methyl-
• CAS No.: 111783-58-5
• Molecular Formula: C10H13N
• Molecular Weight: 147.22
• Mol file: 111783-58-5.mol

Synonyms:

Chemical Property of Benzenemethanamine, 2-ethenyl-N-methyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenemethanamine, 2-ethenyl-N-methyl-

There total 9 articles about Benzenemethanamine, 2-ethenyl-N-methyl- 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: 64.0%

2-chloromethylstyrene (22570-84-9) + methylamine (74-89-5) → N-methyl-1-(2-vinylphenyl)methanamine (111783-58-5)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 0 - 60 ℃; for 4h;

DOI:10.3762/bjoc.15.73

Reference yield:

tricarbonyl(η6-N-methyl-o-vinylbenzylamine)chromium(0) (111741-11-8) → N-methyl-1-(2-vinylphenyl)methanamine (111783-58-5)

Guidance literature:

With oxygen; In diethyl ether; Irradiation (UV/VIS); a soln. of the Cr-compd. is exposed to air and sunlight until the yellow soln. becomes colorless; Cr(III) residues are removed by filtn. and the ether is evapd., further purifn. by flash chromy.;

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → N-methyl-1-(2-vinylphenyl)methanamine (111783-58-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

1.2: Wittig Olefination / 19 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C / Inert atmosphere

3.1: water; methanol / 4 h / 20 °C

4.1: sodium tetrahydroborate / 1 h / 0 - 20 °C

With sodium tetrahydroborate; n-butyllithium; In tetrahydrofuran; methanol; hexane; water; 1.1: |Wittig Olefination;

DOI:10.3987/COM-12-S(N)44

upstream raw materials:

tricarbonyl(η6-N-methyl-o-vinylbenzylamine)chromium(0)

ortho-bromobenzaldehyde

2-bromostyrene

2-vinylbenzaldehyde

Downstream raw materials:

2-methyl-1,2,3,4-tetrahydroisoquinoline

N-methyl-2-(2-((methylamino)methyl)phenyl)-N-(2-vinylbenzyl)ethanamine

Refernces

• 1、 Ogata, Tokutaro,Kimachi, Tetsutaro,Yamada, Ken-Ichi,Yamamoto, Yasutomo,Tomioka, Kiyoshi. "Catalytic asymmetric synthesis of (S)-laudanosine by hydroamination". . p. 469 - 485. Retrieved 2013/08/23.