N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine

Base Information

• Chemical Name: N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine
• CAS No.: 150812-21-8
• Molecular Formula: C13H12FN3O2
• Molecular Weight: 261.256
• Hs Code.: 2921590090
• European Community (EC) Number: 629-884-1
• DSSTox Substance ID: DTXSID80602349
• Wikidata: Q72437201
• Mol file: 150812-21-8.mol

Synonyms:150812-21-8;N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine;1-N-[(4-Fluorophenyl)methyl]-3-nitrobenzene-1,4-diamine;2-Amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene;4-N-[(4-fluorophenyl)methyl]-2-nitrobenzene-1,4-diamine;N1-[(4-fluorophenyl)methyl]-3-nitrobenzene-1,4-diamine;N-(4-Fluorobenzyl)-3-nitro-p-phenylenediamine;N1-(4-Fluorobenzyl)-3-nitro-1,4-phenylenediamine;N4-[(4-Fluorophenyl)methyl]-2-nitro-1,4-benzenediamine;1,4-Benzenediamine, N4-[(4-fluorophenyl)methyl]-2-nitro-;2-amino-5-((4-fluorobenzyl)amino)-1-nitrobenzene;SCHEMBL2236853;DTXSID80602349;XTDZJOIEYRRRGJ-UHFFFAOYSA-N;AMY18442;MFCD12828054;TQ0001;AKOS015853505;AC-5032;HE-0235;4-(4-fluorobenzylamino)-2-nitroaniline;CS-0187565;F1082;A809077;J-523376;N~4~-[(4-Fluorophenyl)methyl]-2-nitrobenzene-1,4-diamine

Chemical Property of N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine

Chemical Property:

• Vapor Pressure: 7.96E-08mmHg at 25°C
• Melting Point: 110.0 to 114.0 °C
• Refractive Index: 1.681
• Boiling Point: 436.6 °C at 760 mmHg
• PKA: 2.08±0.40(Predicted)
• Flash Point: 217.9 °C
• PSA: 83.87000
• Density: 1.39 g/cm³
• LogP: 4.10560
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 261.09135480
• Heavy Atom Count: 19
• Complexity: 303

Purity/Quality:

99% ^*data from raw suppliers

N4-[(4-Fluorophenyl)methyl]-2-nitro-1,4-benzenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CNC2=CC(=C(C=C2)N)[N+](=O)[O-])F
• Uses: Intermediate in the synthesis of Retigabine, a new experimental anticonvulsant drug.

Technology Process of N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine

There total 5 articles about N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-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: 99.6%

→ 1-N-[(4-fluorophenyl)methyl]-3-nitrobenzene-1,4-diamine (150812-21-8)

Guidance literature:

With methanol; sodium tetrahydroborate; In 1,4-dioxane; at 20 ℃;

Reference yield: 94.0%

2-amino-5-(4-fluorobenzylideneamino)nitrobenzene (150812-22-9) → 1-N-[(4-fluorophenyl)methyl]-3-nitrobenzene-1,4-diamine (150812-21-8)

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; methanol; at 20 ℃; for 2h;

DOI:10.1038/aps.2013.79

Reference yield: 85.0%

2-nitro-1,4-phenylenediamine (5307-14-2,183870-67-9) + 4-fluorobenzaldehyde (459-57-4) → 1-N-[(4-fluorophenyl)methyl]-3-nitrobenzene-1,4-diamine (150812-21-8)

Guidance literature:

2-nitro-1,4-phenylenediamine; 4-fluorobenzaldehyde; In isopropyl alcohol; at 75 ℃; for 3h;

With sodium tetrahydroborate; sodium hydroxide; In water; isopropyl alcohol; for 1h;

DOI:10.1021/acs.jmedchem.7b01199

upstream raw materials:

2-nitro-1,4-phenylenediamine

2-amino-5-(4-fluorobenzylideneamino)nitrobenzene

4-fluorobenzaldehyde

Downstream raw materials:

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene

Retigabine

benzyl (4-((ethoxycarbonyl)amino)-3-nitrophenyl)(4-fluorobenzyl)carbamate