4-(2-Phenylethynyl)aniline

Base Information

• Chemical Name: 4-(2-Phenylethynyl)aniline
• CAS No.: 1849-25-8
• Molecular Formula: C14H11N
• Molecular Weight: 193.248
• ChEMBL ID: CHEMBL1542904
• DSSTox Substance ID: DTXSID20404945
• Nikkaji Number: J993.609B
• Wikidata: Q72501858
• Mol file: 1849-25-8.mol

Synonyms:4-(phenylethynyl)aniline;4-(2-phenylethynyl)aniline;1849-25-8;(p-Aminophenyl)phenylacetylene;Benzenamine, 4-(phenylethynyl)-;4-phenylethynyl aniline;MLS000546957;SCHEMBL1009236;(4-aminophenyl)-phenylacetylene;CHEMBL1542904;4-(2-phenyl-1-ethynyl)aniline;DTXSID20404945;ODFQRHOQXHVJTQ-UHFFFAOYSA-N;HMS2413K03;MFCD00168826;AKOS000221757;SMR000180155;CS-0342943;C77994;1T-1154;F2167-5397

Chemical Property of 4-(2-Phenylethynyl)aniline

Chemical Property:

• Melting Point: 126-128℃
• PSA: 26.02000
• Density: 1.13
• LogP: 3.24980
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 193.089149355
• Heavy Atom Count: 15
• Complexity: 243

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(2-PHENYLETHYNYL)ANILINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC2=CC=C(C=C2)N
• Uses: 4-(Phenylethynyl)aniline was synthetically prepared in phosphine-free Sonogashria cross-coupling reactions via palladium(II) phthalocyanine complex catalyst.

Technology Process of 4-(2-Phenylethynyl)aniline

There total 31 articles about 4-(2-Phenylethynyl)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: 99.0%

4-(phenylethynyl)nitrobenzene (1942-30-9) → 4-phenylethynylphenylamine (1849-25-8)

Guidance literature:

With hydrogenchloride; tin; In water; at 60 ℃; for 6h;

DOI:10.1002/chem.201402839

Reference yield: 99.0%

phenylacetylene (536-74-3) + p-aminoiodobenzene (540-37-4) → 4-phenylethynylphenylamine (1849-25-8)

Guidance literature:

With CuI(xantphos); caesium carbonate; In N,N-dimethyl-formamide; at 135 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

DOI:10.1055/s-0031-1290813

Reference yield: 97.0%

phenylpropyolic acid (637-44-5) + p-aminoiodobenzene (540-37-4) → 4-phenylethynylphenylamine (1849-25-8)

Guidance literature:

With copper(l) iodide; potassium carbonate; triphenylphosphine; In water; at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2012.06.003

upstream raw materials:

4-(phenylethynyl)nitrobenzene

copper(I) phenylacetylenide

p-aminoiodobenzene

phenylacetylene

Downstream raw materials:

4-(2-phenylethynyl)benzonitrile

diphenyl acetylene

1-(4-aminophenyl)-2-phenyl-1,2-dicarba-closo-dodecaborane

C₂₆H₂₂N₂O₂S

Refernces

• 1、 Kalashnyk, Nataliya,Ganeshnagaswaran, Praveen,Kervyn, Simon,Riello, Massimo,Moreton, Ben,Jones, Tim S.,Devita, Alessandro,Bonifazi, Davide,Costantini, Giovanni. "Self-assembly of decoupled borazines on metal surfaces: The role of the peripheral groups". . p. 11856 - 11862. Retrieved 2014.
• 2、 Asahara, Haruyasu,Mukaijo, Yusuke,Muragishi, Kengo,Iwai, Kento,Ito, Akitaka,Nishiwaki, Nagatoshi. "Metal-Free and syn-Selective Hydrohalogenation of Alkynes through a Pseudo-Intramolecular Process". . p. 5747 - 5755. Retrieved 2021/10/20.
• 3、 Liu, Qingxiang,Zhang, Xiantao,Zhao, Zhixiang,Li, Xinying,Zhang, Wei. "Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions". supporting information. p. 605 - 613. Retrieved 2021/02/01.