5,6-Dichloro-3-nitropyridin-2-amine

Base Information

• Chemical Name: 5,6-Dichloro-3-nitropyridin-2-amine
• CAS No.: 203794-33-6
• Molecular Formula: C5H3Cl2N3O2
• Molecular Weight: 208.004
• Hs Code.: 2933399090
• European Community (EC) Number: 815-557-2
• DSSTox Substance ID: DTXSID70572320
• Wikidata: Q82460621
• Mol file: 203794-33-6.mol

Synonyms:5,6-Dichloro-3-nitropyridin-2-amine;203794-33-6;2-Pyridinamine, 5,6-dichloro-3-nitro-;MFCD22987594;2-Amino-5,6-dichloro-3-nitropyridine;5,6-Dichloro-2-amino-3-nitropyridine;5,?6-?Dichloro-?3-?nitro-?2-?pyridinamine;SCHEMBL456768;DTXSID70572320;DYSLEQUCBXITJX-UHFFFAOYSA-N;AKOS016012604;AS-63259;SY109206;CS-0037575;EN300-127776;W13138;A849269;F8889-0428

Chemical Property of 5,6-Dichloro-3-nitropyridin-2-amine

Chemical Property:

• Boiling Point: 347.1±37.0 °C(Predicted)
• PKA: -3.87±0.50(Predicted)
• PSA: 84.73000
• Density: 1.723±0.06 g/cm3(Predicted)
• LogP: 2.98320
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 206.9602317
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

98%min ^*data from raw suppliers

5,6-dichloro-3-nitropyridin-2-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=NC(=C1Cl)Cl)N)[N+](=O)[O-]

Technology Process of 5,6-Dichloro-3-nitropyridin-2-amine

There total 1 articles about 5,6-Dichloro-3-nitropyridin-2-amine 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:

6-chloropyridin-2-amine (45644-21-1) → 2-amino-5,6-dichloro-3-nitropyridine (203794-33-6)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 20 h / 20 °C

2: N-chloro-succinimide / N,N-dimethyl-formamide / 16 h / 100 °C

3: hydrogenchloride / ethanol; water / 2 h / 60 °C

4: nitric acid; sulfuric acid / 0.67 h / -10 - 20 °C

With hydrogenchloride; N-chloro-succinimide; sulfuric acid; nitric acid; triethylamine; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bioorg.2020.103580

Reference yield: 71.0%

2-amino-5,6-dichloro-3-nitropyridine (203794-33-6) + 4-(4-morpholinyl)phenylboronic acid (186498-02-2) → C15H15ClN4O3

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In 1,4-dioxane; water; at 100 ℃; for 1h; Inert atmosphere;

Reference yield:

2-amino-5,6-dichloro-3-nitropyridine (203794-33-6) → 5-(biphenyl-4-yl)-6-chloro-2-(methylsulfonyl)-1H-imidazo[4,5-b]pyridine (1394373-37-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium iodide; acetic acid / 2 h / 90 °C

2.1: ethanol / tin(II) chloride hydrate / 0.5 h / 70 °C

3.1: dmap / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.1: potassium hydroxide / ethanol / 0.5 h / 20 °C

4.2: 1 h / 20 °C

5.1: Oxone / acetonitrile; water / 18 h / 20 °C

6.1: potassium phosphate / palladium diacetate; catacxium A / water; tetrahydrofuran / 42 h / 45 °C / Inert atmosphere

With Oxone; potassium phosphate; ethanol; acetic acid; sodium iodide; potassium hydroxide; dmap; tin(II) chloride hydrate; palladium diacetate; catacxium A; In tetrahydrofuran; ethanol; water; acetonitrile;

upstream raw materials:

6-chloropyridin-2-amine

Downstream raw materials:

5,6-dichloropyridine-2,3-diamine

(4-(6-amino-3-chloro-5-nitropyridin-2-yl)piperazin-1-yl)(3-(2-methoxyphenyl)-5-methylisoxazol-4-yl)methanone

(2R,3S,5R)-5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol

(3R,3aR,6R,6aR)-6-[[6-chloro-5-[4-(4-pyrazol-1-ylphenyl)phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

Refernces

• 1、 Papadakis, Georgios,Gerasi, Maria,Snoeck, Robert,Marakos, Panagiotis,Andrei, Graciela,Lougiakis, Nikolaos,Pouli, Nicole. "Synthesis of new imidazopyridine nucleoside derivatives designed as maribavir analogues". . . Retrieved 2020/10/18.