N,N-Dimethyl-4-[(4-nitrophenyl)ethynyl]aniline

Base Information

• Chemical Name: N,N-Dimethyl-4-[(4-nitrophenyl)ethynyl]aniline
• CAS No.: 62197-66-4
• Molecular Formula: C16H14N2O2
• Molecular Weight: 266.299
• DSSTox Substance ID: DTXSID00542990
• Wikidata: Q82419807
• Mol file: 62197-66-4.mol

Synonyms:62197-66-4;N,N-Dimethyl-4-[(4-nitrophenyl)ethynyl]aniline;SCHEMBL10392071;DTXSID00542990;Dimethyl-[4-(4-nitro-phenylethynyl)-phenyl]-amine

Chemical Property of N,N-Dimethyl-4-[(4-nitrophenyl)ethynyl]aniline

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 266.105527694
• Heavy Atom Count: 20
• Complexity: 386

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)C#CC2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of N,N-Dimethyl-4-[(4-nitrophenyl)ethynyl]aniline

There total 14 articles about N,N-Dimethyl-4-[(4-nitrophenyl)ethynyl]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: 86.0%

4-ethynyl-N,N-dimethylaniline (17573-94-3,752235-18-0) + para-nitrophenyl bromide (586-78-7) → bis(p-dimethylaminophenyl)butadiyne (58300-70-2) + 2-(4-(N,N-dimethylamino)phenyl)-1-(4-nitrophenyl)acetylene (62197-66-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(II) sulfate; sodium L-ascorbate; triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo200005n

Reference yield: 68.0%

p-nitrobenzene iodide (636-98-6) + 4-ethynyl-N,N-dimethylaniline (17573-94-3,752235-18-0) → 2-(4-(N,N-dimethylamino)phenyl)-1-(4-nitrophenyl)acetylene (62197-66-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 60 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01598

Reference yield: 64.0%

4-chlorobenzonitrile (100-00-5) + 4-ethynyl-N,N-dimethylaniline (17573-94-3,752235-18-0) → 2-(4-(N,N-dimethylamino)phenyl)-1-(4-nitrophenyl)acetylene (62197-66-4)

Guidance literature:

With (triphenylphosphine)gold(I) chloride; bis(triphenylphosphine)palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; at 100 ℃; for 6h; Inert atmosphere;

DOI:10.1055/s-0032-1318119

upstream raw materials:

N,N-dimethyl-4-[(E)-2-(4-nitrophenyl)vinyl]aniline

4-(4-nitro-phenylethynyl)-aniline

methyl iodide

diethyl p-nitrobenzylphosphonate

Downstream raw materials:

p-(N-methylamino)-p'-nitrodiphenylacetylene