2-(Prop-1-yn-1-yl)aniline

Base Information

• Chemical Name: 2-(Prop-1-yn-1-yl)aniline
• CAS No.: 220465-91-8
• Molecular Formula: C9H9 N
• Molecular Weight: 131.177
• DSSTox Substance ID: DTXSID30444594
• Nikkaji Number: J2.072.743H
• Wikidata: Q82262778
• Mol file: 220465-91-8.mol

Synonyms:220465-91-8;2-(prop-1-yn-1-yl)aniline;2-(1-Propynyl)aniline;2-(1-Propyn-1-yl)aniline;SCHEMBL449613;DTXSID30444594;AKOS006338177

Chemical Property of 2-(Prop-1-yn-1-yl)aniline

Chemical Property:

• Boiling Point: 251.4±23.0 °C(Predicted)
• PKA: 3.41±0.10(Predicted)
• PSA: 26.02000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 2.22140
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 131.073499291
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC1=CC=CC=C1N

Technology Process of 2-(Prop-1-yn-1-yl)aniline

There total 4 articles about 2-(Prop-1-yn-1-yl)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: 100.0%

2-iodophenylamine (615-43-0) + prop-1-yne (74-99-7) → 1-(2-aminophenyl)prop-1-yne (220465-91-8)

Guidance literature:

With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; In triethylamine; at 20 ℃; for 27h;

DOI:10.1021/jo981845k

Reference yield: 66.0%

C14H14N2O2S + calcium carbide (75-20-7) → 1-(2-aminophenyl)prop-1-yne (220465-91-8)

Guidance literature:

With copper(l) iodide; potassium tert-butylate; water; In N,N-dimethyl-formamide; at 90 ℃; for 6h;

DOI:10.1055/s-0037-1610718

Reference yield: 44.0%

2-Butynoic acid (590-93-2) + 2-iodophenylamine (615-43-0) → 1-(2-aminophenyl)prop-1-yne (220465-91-8) + but-2-ynoic acid (2-iodo-phenyl)-amide (705302-06-3)

Guidance literature:

With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 50 ℃; for 2h; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.tetlet.2016.06.073

upstream raw materials:

2-iodophenylamine

prop-1-yne

2-aminoacetophenone

diazomethyl-trimethyl-silane

Downstream raw materials:

2-(1-propynyl)-N-(triphenylphosphoranylidene)benzenamine

3,3′-((4-chlorophenyl)methylene)bis(2-methyl-1H-indole)

bis-(2-methyl-indol-3-yl)-(4-nitro-phenyl)-methane

Refernces

• 1、 Gao, Lei,Li, Zheng. "Direct Synthesis of 1-Arylprop-1-ynes with Calcium Carbide as an Acetylene Source". supporting information. p. 1580 - 1584. Retrieved 2019/08/20.
• 2、 Maaliki, Carine,Chevalier, Yoan,Thiery, Emilie,Thibonnet, Jér?me. "Palladium and copper catalyzed Sonogashira decarboxylative coupling of aryl iodides and alkynyl carboxylic acids". supporting information. p. 3358 - 3362. Retrieved 2016/07/11.