n,n-Dimethyl-4-(1-phenylethenyl)aniline

Base Information

• Chemical Name: n,n-Dimethyl-4-(1-phenylethenyl)aniline
• CAS No.: 22057-80-3
• Molecular Formula: C16H17 N
• Molecular Weight: 223.318
• NSC Number: 157904
• DSSTox Substance ID: DTXSID50303336
• Nikkaji Number: J1.194.694A,J2.612.443C
• Wikidata: Q82048544
• ChEMBL ID: CHEMBL1564216
• Mol file: 22057-80-3.mol

Synonyms:n,n-dimethyl-4-(1-phenylethenyl)aniline;22057-80-3;NSC 157904;N,N-dimethyl-N-[4-(1-phenylvinyl)phenyl]amine;NSC157904;MLS001195064;SCHEMBL607222;CHEMBL1564216;DTXSID50303336;HMS1607E08;HMS2854H24;alpha-Phenyl-4-(dimethylamino)styrene;CCG-103206;NSC-157904;SMR000554451;1-(4-dimethylaminophenyl)-1-phenylethylene;1-(p-dimethylaminophenyl)-1-phenylethylene;EU-0066834;1-[4-(Dimethylamino)phenyl]-1-phenylethylene;SR-01000389615;SR-01000389615-1

Chemical Property of n,n-Dimethyl-4-(1-phenylethenyl)aniline

Chemical Property:

• Vapor Pressure: 3.66E-05mmHg at 25°C
• Boiling Point: 353.1°C at 760 mmHg
• Flash Point: 143.5°C
• Density: 1.015g/cm³
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 223.136099547
• Heavy Atom Count: 17
• Complexity: 242

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)C(=C)C2=CC=CC=C2

Technology Process of n,n-Dimethyl-4-(1-phenylethenyl)aniline

There total 14 articles about n,n-Dimethyl-4-(1-phenylethenyl)aniline 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: 91.0%

1-bromovinylbenzene (98-81-7) + 4-(dimethylamino)benzene-boronic acid (28611-39-4) → 1-[4-(dimethylamino)phenyl]-1-phenylethene (22057-80-3)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); Tedicyp; potassium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 20h;

DOI:10.1002/ejoc.200390161

Reference yield: 84.0%

triphenylboroxine (3262-89-3) + 4'-dimethylaminoacetophenone (2124-31-4) → 1-[4-(dimethylamino)phenyl]-1-phenylethene (22057-80-3)

Guidance literature:

With tetrakis(triphenylphosphine)nickel⁽⁰⁾; water; 1,2-bis-(dicyclohexylphosphino)ethane; In diethylene glycol dimethyl ether; at 120 ℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.7b02742

Reference yield: 82.0%

4-bromo-N,N-dimethylaniline (586-77-6) + Cinnamic acid (621-82-9) → 1-[4-(dimethylamino)phenyl]-1-phenylethene (22057-80-3)

Guidance literature:

Cinnamic acid; With potassium tert-butylate; In ethanol; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

4-bromo-N,N-dimethylaniline; With palladium(II) acetylacetonate; 1,10-Phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide; In 1-methyl-pyrrolidin-2-one; quinoline; ethanol; at 170 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201605744

upstream raw materials:

methyl magnesium iodide

4-(Dimethylamino)benzophenone

1,1-bis-(4-dimethylamino-phenyl)-1-phenyl-ethane

1-[4-(dimethylamino)phenyl]-1-phenylethanol

Downstream raw materials:

N,N-dimethyl-4-(1-phenylethyl)aniline

5-(4-dimethylamino-phenyl)-5-phenyl-penta-2,4-dienal

4'-Chloro-4-dimethylaminoazobenzene

N,N-dimethyl-4-[(E)-(4-nitrophenyl)diazenyl]aniline

Refernces

• 1、 Ritz, Mikhaila D.,Parsons, Astrid M.,Palermo, Philip N.,Jones, William D.. "Bisoxazoline-pincer ligated cobalt-catalyzed hydrogenation of alkenes". supporting information. . Retrieved 2020/02/13.
• 2、 Tang, Jie,Hackenberger, Dagmar,Goossen, Lukas J.. "Branched Arylalkenes from Cinnamates: Selectivity Inversion in Heck Reactions by Carboxylates as Deciduous Directing Groups". supporting information. p. 11296 - 11299. Retrieved 2016/10/13.