4-AMino-6-chloro-3-nitro-2-pyridinecarbonitrile

Base Information

• Chemical Name: 4-AMino-6-chloro-3-nitro-2-pyridinecarbonitrile
• CAS No.: 944388-71-0
• Molecular Formula: C6H3ClN4O2
• Molecular Weight: 198.568
• Mol file: 944388-71-0.mol

Synonyms:4-AMino-6-chloro-3-nitro-2-pyridinecarbonitrile

Chemical Property of 4-AMino-6-chloro-3-nitro-2-pyridinecarbonitrile

Chemical Property:

• Boiling Point: 488.3±45.0 °C (760 mmHg)
• PSA: 108.52000
• Density: 1.65±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: 2.20148

Purity/Quality:

98% ^*data from raw suppliers

4-Amino-6-chloro-3-nitro-2-pyridinecarbonitrile 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-AMino-6-chloro-3-nitro-2-pyridinecarbonitrile

There total 11 articles about 4-AMino-6-chloro-3-nitro-2-pyridinecarbonitrile 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: 80.0%

2,6-dichloro-3-nitropyridin-4-amine (2897-43-0) → 4-amino-6-chloro-3-nitropyridine-2-carbonitrile (944388-71-0)

Guidance literature:

With copper(l) cyanide; In 1-methyl-pyrrolidin-2-one; at 180 ℃;

DOI:10.1016/j.bmcl.2010.06.072

Reference yield:

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 4-amino-6-chloro-3-nitropyridine-2-carbonitrile (944388-71-0)

Guidance literature:

Multi-step reaction with 7 steps

1: oxalyl dichloride / dichloromethane; tetrahydrofuran / 4 h / 25 °C

2: sodium azide / water; acetone / 0.03 h / 25 °C

3: trifluoroacetic acid / benzene / 21 h / 90 °C

4: potassium carbonate / methanol / 7.5 h / 25 °C

5: sulfuric acid; nitric acid / -5 °C

6: sulfuric acid / 1 h / 0 - 100 °C

7: 1-methyl-pyrrolidin-2-one / 0.67 h / 180 °C

With sodium azide; oxalyl dichloride; sulfuric acid; nitric acid; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; acetone; benzene; 3: |Curtius Rearrangement;

DOI:10.1002/cmdc.201300112

Reference yield:

copper(I) cyanide (544-92-3) + 2,6-dichloro-3-nitropyridin-4-amine (2897-43-0) → 4-amino-6-chloro-3-nitropyridine-2-carbonitrile (944388-71-0)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 180 ℃; for 0.2h;

upstream raw materials:

copper(I) cyanide

2,6-dichloro-3-nitropyridin-4-amine

methyl 2,6-dichloroisonicotinate

citrazinic acid

Downstream raw materials:

4-amino-6-(4-methoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile

4-amino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile

6-[(1,3-benzodioxol-5-ylmethyl)(cyclohexyl)amino]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

4-amino-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridine-2-carbonitrile

Refernces

• 1、 Cai, Jiaqiang,Baugh, Mark,Black, Darcey,Long, Clive,Jonathan Bennett,Dempster, Maureen,Fradera, Xavier,Gillespie, Jonathan,Andrews, Fiona,Boucharens, Sylviane,Bruin, John,Cameron, Kenneth S.,Cumming, Iain,Hamilton, William,Jones, Philip S.,Kaptein, Allard,Kinghorn, Emma,Maidment, Maurice,Martin, Iain,Mitchell, Ann,Rankovic, Zoran,Robinson, John,Scullion, Paul,Uitdehaag, Joost C.M.,Vink, Paul,Westwood, Paul,Van Zeeland, Mario,Van Berkom, Leon,Bastiani, Martijn,Meulemans, Tommi. "6-Phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile as cathepsin S inhibitors". scheme or table. p. 4350 - 4354. Retrieved 2010/09/11.
• 2、 -. "6-PHENYL-1H-IMIDAZO[4,5-c]PYRIDINE-4-CARBONITRILE DERIVATIVES". Page/Page column 9. . Retrieved 2009/04/24.