5-Chloro-2-(pyridin-2-yl)aniline

Base Information

• Chemical Name: 5-Chloro-2-(pyridin-2-yl)aniline
• CAS No.: 113623-77-1
• Molecular Formula: C11H9ClN2
• Molecular Weight: 204.659
• DSSTox Substance ID: DTXSID80552557
• Wikidata: Q82432890
• Mol file: 113623-77-1.mol

Synonyms:113623-77-1;5-Chloro-2-(pyridin-2-yl)aniline;SCHEMBL3091852;DTXSID80552557;SXIVLZSNPQOKIU-UHFFFAOYSA-N;5-chloro-2-(2-pyridin-yl)-aniline;AKOS019846557

Chemical Property of 5-Chloro-2-(pyridin-2-yl)aniline

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 204.0454260
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C2=C(C=C(C=C2)Cl)N

Technology Process of 5-Chloro-2-(pyridin-2-yl)aniline

There total 7 articles about 5-Chloro-2-(pyridin-2-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: 76.0%

2-(4-Chloro-2-nitrophenyl)pyridine (4381-28-6) → 5-chloro-2-(pyridin-2-yl)benzenamine (113623-77-1)

Guidance literature:

With hydrogenchloride; for 2h;

Reference yield: 75.3%

2-bromo-pyridine (109-04-6) + 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzenamine (863578-21-6) → 5-chloro-2-(pyridin-2-yl)benzenamine (113623-77-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; water; at 100 ℃; for 12h;

DOI:10.1021/acsmedchemlett.6b00328

Reference yield:

2-bromo-5-chloroaniline (823-57-4) → 5-chloro-2-(pyridin-2-yl)benzenamine (113623-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / 12 h / 100 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; In 1,2-dimethoxyethane; water; dimethyl sulfoxide; 2: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.6b00328

upstream raw materials:

2-(4-Chloro-2-nitrophenyl)pyridine

pyridine

4-Chloro-2-nitroaniline

2-bromo-5-chloroaniline

Downstream raw materials:

4-chloro-N-[5-chloro-2-pyridin-2-yl-phenyl]-3-trifluoromethylbenzenesulfonamide

[2-(5-Chloro-2-pyridin-2-yl-phenylcarbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester