Benzenamine, N,N-dimethyl-4-[(1E)-2-phenyl-1-propenyl]-

Base Information

• Chemical Name: Benzenamine, N,N-dimethyl-4-[(1E)-2-phenyl-1-propenyl]-
• CAS No.: 83832-02-4
• Molecular Formula: C17H19N
• Molecular Weight: 237.345
• Mol file: 83832-02-4.mol

Synonyms:

Chemical Property of Benzenamine, N,N-dimethyl-4-[(1E)-2-phenyl-1-propenyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenamine, N,N-dimethyl-4-[(1E)-2-phenyl-1-propenyl]-

There total 3 articles about Benzenamine, N,N-dimethyl-4-[(1E)-2-phenyl-1-propenyl]- 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: 84.0%

N,N-dimethyl-aniline (121-69-7,77733-26-7) + isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6) → (E)-N,N-dimethyl-4-(2-phenylprop-1-en-1-yl)aniline (83832-02-4)

Guidance literature:

With copper diacetate; palladium diacetate; In acetic acid; 1,2-dichloro-ethane; at 60 ℃; for 5h; regioselective reaction; Sealed tube;

DOI:10.1021/acs.joc.7b01570

Reference yield: 76.0%

N,N-dimethyl-4-(2-phenylallyl)aniline → (E)-N,N-dimethyl-4-(2-phenylprop-1-en-1-yl)aniline (83832-02-4)

Guidance literature:

With borane-ammonia complex; (3aR,7aR)-1,3-diisopropyl-2-((2-((E)-(quinolin-2-ylmethylene)amino)phenyl)amino)octahydro-1H-benzo[d][1,3,2]diazaphosphole 2-oxide; cobalt(II) bromide; sodium t-butanolate; In toluene; at 60 ℃; for 12h; stereoselective reaction; Glovebox; Inert atmosphere;

DOI:10.1021/jacs.0c02101

Reference yield:

1-phenyl-2-<4-(N,N-dimethylamino)phenyl>ethanone (6266-95-1) → (E)-N,N-dimethyl-4-(2-phenylprop-1-en-1-yl)aniline (83832-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 1 h / 50 °C / Inert atmosphere

2.1: (3aR,7aR)-1,3-diisopropyl-2-((2-((E)-(quinolin-2-ylmethylene)amino)phenyl)amino)octahydro-1H-benzo[d][1,3,2]diazaphosphole 2-oxide; cobalt(II) bromide; sodium t-butanolate; borane-ammonia complex / toluene / 12 h / 60 °C / Glovebox; Inert atmosphere

With borane-ammonia complex; potassium tert-butylate; (3aR,7aR)-1,3-diisopropyl-2-((2-((E)-(quinolin-2-ylmethylene)amino)phenyl)amino)octahydro-1H-benzo[d][1,3,2]diazaphosphole 2-oxide; cobalt(II) bromide; sodium t-butanolate; In tetrahydrofuran; toluene; 1.1: |Wittig Olefination;

DOI:10.1021/jacs.0c02101

upstream raw materials:

N,N-dimethyl-aniline

isopropenylbenzene

1-phenyl-2-<4-(N,N-dimethylamino)phenyl>ethanone

Refernces

• 1、 Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh,Karimi, Ashkan. "Oxidative heck reaction as a tool for para-selective olefination of aniline: A DFT supported mechanism". . p. 10635 - 10640. Retrieved 2018/05/31.