2-(2-Phenylethynyl)aniline

Base Information

• Chemical Name: 2-(2-Phenylethynyl)aniline
• CAS No.: 13141-38-3
• Molecular Formula: C14H11N
• Molecular Weight: 193.248
• Hs Code.: 2921490090
• European Community (EC) Number: 835-193-8
• Nikkaji Number: J546.176F
• Pharos Ligand ID: XDYH3PLTUYYA
• ChEMBL ID: CHEMBL1565578
• Mol file: 13141-38-3.mol

Synonyms:2-(2-phenylethynyl)aniline;2-(phenylethynyl)aniline;13141-38-3;2-Phenylethynyl-phenylamine;UPCMLD00CC-135;MFCD00168849;MLS000544255;SCHEMBL929235;2-(2-Phenylethynyl)benzenamine;CHEMBL1565578;BZDTZZOSIAUOBS-UHFFFAOYSA-N;HMS2203D07;HMS3343O05;1-(2-Aminophenyl)-2-phenylethyne;UPCMLD00CC-135:002;CMLD4_000166;STK006694;AKOS000221756;SDCCGMLS-0091415.P001;NCGC00074310-01;Acetylene, 1-(2-aminophenyl)-2-phenyl-;DS-10387;SMR000163894;SY115556;CS-0156580;EN300-97706;F21387;10.14272/BZDTZZOSIAUOBS-UHFFFAOYSA-N.1;AI-034/31406014;doi:10.14272/BZDTZZOSIAUOBS-UHFFFAOYSA-N.1;F2167-5395;Z332376762

Chemical Property of 2-(2-Phenylethynyl)aniline

Chemical Property:

• Melting Point: 89 °C(Solv: ethanol (64-17-5))
• Boiling Point: 156 - 158 °C (2 mmHg)
• PKA: 2.42±0.10(Predicted)
• PSA: 26.02000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.24980
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 193.089149355
• Heavy Atom Count: 15
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

2-Phenylethynyl-Phenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC2=CC=CC=C2N

Technology Process of 2-(2-Phenylethynyl)aniline

There total 42 articles about 2-(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%

2-ethynylaniline (52670-38-9) + iodobenzene (591-50-4) → 2-phenylethynylaniline (13141-38-3)

Guidance literature:

With pyrrolidine; at 85 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2008.10.130

Reference yield: 95.0%

2-iodophenylamine (615-43-0) + prop-1-yne (74-99-7) → 2-phenylethynylaniline (13141-38-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 0.833333h; Inert atmosphere;

DOI:10.1002/chem.202002581

Reference yield: 89.0%

1-bromo-2-(phenylethenyl)benzene (21375-88-2) → 2-phenylethynylaniline (13141-38-3)

Guidance literature:

With (R)-1-[(S_P)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; ammonia; sodium t-butanolate; In 1,4-dioxane; at 90 ℃; for 18h; Inert atmosphere;

DOI:10.1039/c1cc11874a

upstream raw materials:

1-nitro-2-phenylethynyl-benzene

2-iodophenylamine

phenylacetylene

copper(I) phenylacetylenide

Downstream raw materials:

3-phenyl-1H-quinolin-2-one

3-benzyl-2-oxindole

(3E)-3-benzylidene-1,3-dihydro-2H-indol-2-one

4-chloro-3-phenylcinnoline

Refernces

• 1、 Nasseri, Mohammad Ali,Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Allahresani, Ali. "The CuFe2O4@SiO2@ZrO2/SO42-/Cu nanoparticles: An efficient magnetically recyclable multifunctional Lewis/Br?nsted acid nanocatalyst for the ligand- and Pd-free Sonogashira cross-coupling reaction in water". . p. 20749 - 20759. Retrieved 2019.
• 2、 Majumdar,Samanta,Chattopadhyay. "A convenient synthesis of pyrrolopyridines and 2-substituted indoles by gold-catalyzed cycloisomerization". . p. 7213 - 7216. Retrieved 2008.
• 3、 Fang, Xiaolan,Cao, Ji,Ding, Weijie,Jin, Huile,Yu, Xiaochun,Wang, Shun. "Copper-Catalyzed Aerobic Oxidative Cyclization of 2-Alkynylanilines with Nitrosoarenes: Synthesis of Organic Solid Mechanoluminescence Compounds of 4-Oxo-4 H-cinnolin-2-ium-1-ide". supporting information. p. 1228 - 1233. Retrieved 2021/02/20.
• 4、 Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat. "A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water". . p. 10645 - 10660. Retrieved 2020/09/18.