2,4-dichloro-6-ethynyl-aniline

Base Information

• Chemical Name: 2,4-dichloro-6-ethynyl-aniline
• CAS No.: 684250-09-7
• Molecular Formula: C8H5Cl2N
• Molecular Weight: 186.04
• Mol file: 684250-09-7.mol

Synonyms:

Chemical Property of 2,4-dichloro-6-ethynyl-aniline

Chemical Property:

• Vapor Pressure: 0.00267mmHg at 25°C

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,4-dichloro-6-ethynyl-aniline

There total 3 articles about 2,4-dichloro-6-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%

2,4-dichloro-6-trimethylsilanylethynylaniline (684250-19-9) → 2,4-dichloro-6-ethynylphenylamine (684250-09-7)

Guidance literature:

With potassium fluoride; In methanol; at 20 ℃; for 3h;

DOI:10.1055/s-2004-815947

Reference yield:

2,4-dichloro-6-bromoaniline (697-86-9) → 2,4-dichloro-6-ethynylphenylamine (684250-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N / PdCl₂(PPh₃)2; CuI / dimethylformamide / 8 h / 50 °C

2: 86 percent / KF / methanol / 3 h / 20 °C

With potassium fluoride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In methanol; N,N-dimethyl-formamide; 1: Sonogashira reaction;

DOI:10.1055/s-2004-815947

Reference yield:

2,4-dichloro-6-iodoaniline (697-90-5) → 2,4-dichloro-6-ethynylphenylamine (684250-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 2 h / 20 °C

2: potassium carbonate; methanol / 2 h / 20 °C

With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine;

DOI:10.1039/c4cc03565h

upstream raw materials:

2,4-dichloro-6-trimethylsilanylethynylaniline

2,4-dichloro-6-bromoaniline

2,4-dichloro-6-iodoaniline

Downstream raw materials:

5,7-dichloro-1-tosylindolin-3-one

N-(2,4-dichloro-6-ethynylphenyl)-4-methylbenzenesulfonamide

5,7-dibromo-2-phenyl-1H-indole

5,7-dichloro-3-fluoro-2-phenyl-1H-indole

Refernces

• 1、 Arcadi, Antonio,Bianchi, Gabriele,Marinelli, Fabio. "Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles". . p. 610 - 618. Retrieved 2007/10/03.