4-[2-(4-Aminophenyl)ethynyl]aniline

Base Information

• Chemical Name: 4-[2-(4-Aminophenyl)ethynyl]aniline
• CAS No.: 6052-15-9
• Molecular Formula: C14H12N2
• Molecular Weight: 208.263
• Hs Code.: 2921499090
• DSSTox Substance ID: DTXSID50363394
• Nikkaji Number: J677.591H
• Wikidata: Q82147064
• Pharos Ligand ID: 151SZ5BJXFW6
• ChEMBL ID: CHEMBL227625
• Mol file: 6052-15-9.mol

Synonyms:6052-15-9;4-[2-(4-aminophenyl)ethynyl]aniline;4,4'-(Ethyne-1,2-diyl)dianiline;Bis(4-aminophenyl)acetylene;Benzenamine,4,4'-(1,2-ethynediyl)bis-;CHEMBL227625;Diaminotolan;4,4'-Ethynylenedianiline;YSZC057;SCHEMBL864945;DTXSID50363394;BDBM50476290;MFCD00458961;AKOS004901015;4,4'-(1,2-ethynediyl)bis-Benzenamine;CS-0110599;FT-0768581;9M-704;D84228;A904507;J-513241

Chemical Property of 4-[2-(4-Aminophenyl)ethynyl]aniline

Chemical Property:

• Melting Point: 238-242°C
• Boiling Point: 429.7 °C at 760 mmHg
• PKA: 4.25±0.10(Predicted)
• Flash Point: 256 °C
• PSA: 52.04000
• Density: 1.2g/cm³
• LogP: 3.41320
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 208.100048391
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

98%Min ^*data from raw suppliers

4,4'-(Ethyne-1,2-diyl)dianiline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#CC2=CC=C(C=C2)N)N

Technology Process of 4-[2-(4-Aminophenyl)ethynyl]aniline

There total 9 articles about 4-[2-(4-Aminophenyl)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: 92.0%

p-aminoiodobenzene (540-37-4) + acetylene (74-86-2,25067-58-7) → 4,4'-(ethyne-1,2-diyl)dianiline (6052-15-9)

Guidance literature:

With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In 1,4-dioxane; water; at 80 ℃; for 15h;

DOI:10.5012/bkcs.2010.31.7.2097

Reference yield: 88.0%

4-Ethynylaniline (14235-81-5) + p-aminoiodobenzene (540-37-4) → 4,4'-(ethyne-1,2-diyl)dianiline (6052-15-9)

Guidance literature:

With C₁₆H₂₀Cl₂N₂O₂Pd; potassium hydroxide; In water; acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2015.12.086

Reference yield: 76.0%

4-Ethynylaniline (14235-81-5) + 4-bromo-aniline (106-40-1) → 4,4'-(ethyne-1,2-diyl)dianiline (6052-15-9)

Guidance literature:

4-bromo-aniline; With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; BH₄^(1-)*C₁₂H₂₇P*H⁽¹⁺⁾; diisopropylamine; In 1,4-dioxane; for 0.25h; Schlenk technique; Sealed tube;

4-Ethynylaniline; In 1,4-dioxane; at 20 ℃; Schlenk technique;

DOI:10.1002/asia.202100530

upstream raw materials:

1,2-bis(4-nitrophenyl)acetylene

4-(4-nitro-phenylethynyl)-aniline

4-(prop-1-yn-1-yl)aniline

4-Ethynylaniline

Downstream raw materials:

1,2-bis(4-iodophenyl)acetylene

C₁₁₀H₉₀N₄O₁₂

bis-(4-acetylamino-phenyl)-acetylene

4,4'-diaminodeoxybenzoin

Refernces

• 1、 Abdallah, Mennatallah,Hamed, Mostafa M.,Frakolaki, Efseveia,Katsamakas, Sotirios,Vassilaki, Niki,Bartenschlager, Ralf,Zoidis, Grigoris,Hirsch, Anna K.H.,Abdel-Halim, Mohammad,Abadi, Ashraf H.. "Redesigning of the cap conformation and symmetry of the diphenylethyne core to yield highly potent pan-genotypic NS5A inhibitors with high potency and high resistance barrier". . . Retrieved 2021/12/27.
• 2、 Li, Jiahua,Wang, Zitong,Sun, Zelin,Xu, Linli,Wong, Wai-Yeung. "Effect of the Linking Group on the Thermoelectric Properties of Poly(Schiff Base)s and Their Metallopolymers". supporting information. p. 1911 - 1917. Retrieved 2021/06/21.