2-(2,6-Dimethyl-phenoxy)-5-nitropyridine

Base Information

• Chemical Name: 2-(2,6-Dimethyl-phenoxy)-5-nitropyridine
• CAS No.: 76893-49-7
• Molecular Formula: C₁₃H₁₂N₂O₃
• Molecular Weight: 244.25
• DSSTox Substance ID: DTXSID001278656
• Mol file: 76893-49-7.mol

Synonyms:2-(2,6-Dimethyl-phenoxy)-5-nitropyridine;76893-49-7;SCHEMBL1979539;MVNSRPAQFQYAIQ-UHFFFAOYSA-N;DTXSID001278656;2-(2,6-dimethylphenoxy)-5-nitropyridine;2-[(2,6-dimethylphenyl)oxy]-5-nitropyridine

Chemical Property of 2-(2,6-Dimethyl-phenoxy)-5-nitropyridine

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 244.08479225
• Heavy Atom Count: 18
• Complexity: 283

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)OC2=NC=C(C=C2)[N+](=O)[O-]

Technology Process of 2-(2,6-Dimethyl-phenoxy)-5-nitropyridine

There total 1 articles about 2-(2,6-Dimethyl-phenoxy)-5-nitropyridine 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: 84.0%

2-chloro-5-nitropyridine (4548-45-2) + 2.6-dimethylphenol (576-26-1,25134-01-4) → 2-[(2,6-dimethylphenyl)oxy]-5-nitropyridine (76893-49-7)

Guidance literature:

With sodium hydroxide; tetrabutyl-ammonium chloride; In water; benzene; at 50 ℃; for 2h;

DOI:10.1055/s-1980-29272

Reference yield:

2-[(2,6-dimethylphenyl)oxy]-5-nitropyridine (76893-49-7) → 6-[(2,6-dimethylphenyl)oxy]-3-pyridinamine (928003-13-8)

Guidance literature:

With hydrazine hydrate; palladium on carbon; In ethanol; at 90 ℃; for 3h;

Reference yield:

2-[(2,6-dimethylphenyl)oxy]-5-nitropyridine (76893-49-7) → (5R)-3-{6-[(2,6-dimethylphenyl)oxy]-3-pyridinyl}-5-methyl-2,4-imidazolidinedione (1311136-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrazine hydrate / palladium on carbon / ethanol / 3 h / 90 °C

2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C

2.2: 4 h / 20 - 60 °C

3.1: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C

4.1: dmap; triethylamine / dichloromethane / 0.33 h / 0 °C

With dmap; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; palladium on carbon; In ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

2-chloro-5-nitropyridine

2.6-dimethylphenol

Downstream raw materials:

1,1-dimethylethyl [2-({6-[(2,6-dimethylphenyl)oxy]-3-pyridinyl}amino)-1,1-dimethyl-2-oxoethyl]carbamate

N'-{6-[(2,6-dimethylphenyl)oxy]-3-pyridinyl}-2-methylalaninamide

(5R)-3-{6-[(2,6-dimethylphenyl)oxy]-3-pyridinyl}-5-methyl-2,4-imidazolidinedione

3-{6-[(2,6-dimethylphenyl)oxy]-3-pyridinyl}-5,5-dimethyl-2,4-imidazolidinedione

Refernces

• 1、 Alsaidi, Hattab,Gallo, Roger,Metzger, Jacques. "Convenient Synthesis of Heteroaryl Phenyl Ethers from Chloropyridines and Chloroquinolines using Phase-Transfer Catalysis". . p. 921 - 924. Retrieved 2007/10/02.