N6-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine

Base Information

• Chemical Name: N6-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine
• CAS No.: 33400-49-6
• Molecular Formula: C12H11FN4O2
• Molecular Weight: 262.243
• Hs Code.: 2933399090
• European Community (EC) Number: 251-498-3
• DSSTox Substance ID: DTXSID60187048
• Nikkaji Number: J308.482E
• Wikidata: Q72440014
• Mol file: 33400-49-6.mol

Synonyms:33400-49-6;N2-(4-Fluorobenzyl)-5-nitropyridine-2,6-diamine;2-amino-3-nitro-6-(4-fluorobenzylamino)pyridine;2-AMINO-6-(4-FLUOROBENZYLAMINO)-3-NITROPYRIDINE;N6-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine;6-N-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine;EINECS 251-498-3;2,6-Pyridinediamine, N6-[(4-fluorophenyl)methyl]-3-nitro-;MFCD08282317;2-Amino-6-[(4-fluorobenzyl)-amino]-3-nitropyridine;N6-((4-Fluorophenyl)methyl)-3-nitropyridine-2,6-diamine;2-Amino-3-nitro-6-(4-fluorobenzyl amino)pyridine;4-Methyl-pyrimidin-5-ylamine;SCHEMBL317861;DTXSID60187048;N6-[(4-Fluorophenyl)methyl]-3-nitro-2,6-pyridinediamine;BCP12986;CS-D0700;Propiolic Acid Sodium Salt (90%);C12-H11-F-N4-O2;AKOS015918315;CS-T-03144;AC-23934;CS-11580;SY025654;A5953;FT-0655326;AU-065/43519158;2-Amino-3-nitro-6-(4'-fluorobenzylamino)-pyridine;J-019177;J-523401;N^6^-(4-Fluorobenzyl)-3-nitropyridine-2,6-diamine;N~6~-(4-fluorobenzyl)-3-nitro-2,6-pyridinediamine;N6-(4-Fluoro-benzyl)-3-nitro-pyridine-2,6-diamine;2-AMINO-3-NITRO-6-(4-FLUORBENZYLAMINO)-PYRIDINE;6-[[(4-Fluorophenyl)methyl]amino]-3-nitro-2-pyridinamine;N6-[(4-Fluorophenyl)methyl]-3-nitro-pyridine-2,6-diamine;2,6-Pyridinediamine, N(6)-((4-fluorophenyl)methyl)-3-nitro-;2-Amino-3-nitro-6-(4-fluorobenzylamino)pyridine, AldrichCPR;2-AMINO-3-NITRO-6-(4'-FLUORBENZYLAMINO)-PYRIDINE SPECIALITY CHEMICALS;2-amino-3-nitro-6-(4 inverted exclamation mark(R)-fluorbenzylamino)-pyridine speciality chemicals

Chemical Property of N6-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 8.35E-09mmHg at 25°C
• Refractive Index: 1.689
• Boiling Point: 464.5 °C at 760 mmHg
• PKA: 1.52±0.50(Predicted)
• Flash Point: 234.7 °C
• PSA: 96.76000
• Density: 1.448 g/cm³
• LogP: 3.50060
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 262.08660377
• Heavy Atom Count: 19
• Complexity: 305

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-6-[(4-fluorobenzyl)-amino]-3-nitropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CNC2=NC(=C(C=C2)[N+](=O)[O-])N)F
• Uses: Intermediate in the preparation of Flupirtine metabolites.

Technology Process of N6-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine

There total 2 articles about N6-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine 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: 99.0%

2-amino-6-chloro-3-nitropyridine (27048-04-0) + para-fluorobenzylamine (140-75-0) → 2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine (33400-49-6)

Guidance literature:

With triethylamine; In isopropyl alcohol; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01199

Reference yield:

2,6-dicholoro-3-nitropyridine (16013-85-7,136901-10-5) → 2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine (33400-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia

2: triethylamine / dioxane

With ammonia; triethylamine; In 1,4-dioxane;

DOI:10.1021/jm00045a005

Reference yield: 98.6%

2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine (33400-49-6) → 6-amino-2-(4-fluorobenzylamino)-3-bromo-5-nitropyridine (1422275-78-2)

Guidance literature:

With N-Bromosuccinimide; ammonium acetate; In tetrahydrofuran; acetonitrile; at 0 ℃; for 3h;

DOI:10.5560/ZNB.2012-0258

upstream raw materials:

2-amino-6-chloro-3-nitropyridine

para-fluorobenzylamine

2,6-dicholoro-3-nitropyridine

Downstream raw materials:

N⁶-(4-fluorobenzyl)pyridine-2,3,6-triamine

flupirtine hydrochloride

flupirtine maleate

Refernces

• 1、 -. "A flupirtin derivative and its inorganic acid salt preparation method (by machine translation)". Paragraph 0052-0056; 0065-0067; 0076-0078. . Retrieved 2019/10/22.
• 2、 Kinarivala, Nihar,Patel, Ronak,Boustany, Rose-Mary,Al-Ahmad, Abraham,Trippier, Paul C.. "Discovery of Aromatic Carbamates that Confer Neuroprotective Activity by Enhancing Autophagy and Inducing the Anti-Apoptotic Protein B-Cell Lymphoma 2 (Bcl-2)". . p. 9739 - 9756. Retrieved 2017/12/26.