6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 178269-03-9
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.162
• DSSTox Substance ID: DTXSID30440672
• Mol file: 178269-03-9.mol

Synonyms:178269-03-9;6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine;1H-PYRROLO[2,3-B]PYRIDINE, 6-METHYL-3-NITRO-;6-Methyl-3-nitro-7-azaindole;DTXSID30440672;AKOS006312991;SB14333;CS-0004102;1H-Pyrrolo[2,3-b]pyridine,6-methyl-3-nitro-;A881407;1H-PYRROLO[2,3-B]PYRIDINE,6-METHYL-3-NITRO

Chemical Property of 6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.707
• Boiling Point: 362.183°C at 760 mmHg
• Flash Point: 172.842°C
• PSA: 74.50000
• Density: 1.438g/cm³
• LogP: 2.30270
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 177.053826475
• Heavy Atom Count: 13
• Complexity: 216

Purity/Quality:

95% ^*data from raw suppliers

6-Methyl-3-nitro-7-azaindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2=C(C=C1)C(=CN2)[N+](=O)[O-]

Technology Process of 6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine

There total 4 articles about 6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine 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-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxide (178268-96-7) → 6-Methyl-4-nitro-1H-pyrrolo[2,3-b]pyridine + 6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine (178269-03-9)

Guidance literature:

With nitric acid; trifluoroacetic acid; phosphorus trichloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) 0 deg C, 2.) chloroform, reflux, 2 h;

DOI:10.1002/jhet.5570330215

Reference yield:

2-amino-3,6-dimethylpyridine (823-61-0) → 6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine (178269-03-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / PCl₅ / CHCl₃ / 3 h / Heating

2: NaH, N-methylaniline / Heating

3: 14 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 20 h / Ambient temperature

4: 1.) HNO₃, trifluoroacetic acid, 2.) PCl₃ / 1.) 0 deg C, 2.) chloroform, reflux, 2 h

With phosphorus pentachloride; nitric acid; sodium hydride; 3-chloro-benzenecarboperoxoic acid; N-methylaniline; trifluoroacetic acid; phosphorus trichloride; In dichloromethane; chloroform;

DOI:10.1002/jhet.5570330215

Reference yield:

6-methyl-1H-pyrrolo<2,3-b>pyridine (824-51-1) → 6-Methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine (178269-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 14 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 20 h / Ambient temperature

2: 1.) HNO₃, trifluoroacetic acid, 2.) PCl₃ / 1.) 0 deg C, 2.) chloroform, reflux, 2 h

With nitric acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; phosphorus trichloride; In dichloromethane;

DOI:10.1002/jhet.5570330215

upstream raw materials:

6-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxide

2-amino-3,6-dimethylpyridine

6-methyl-1H-pyrrolo<2,3-b>pyridine

N'-(3,6-Dimethyl-pyridin-2-yl)-N-methyl-N-phenyl-formamidine

Refernces