4-(4-Fluorobenzylamino)-1,2-phenylenediamine

Base Information

• Chemical Name: 4-(4-Fluorobenzylamino)-1,2-phenylenediamine
• CAS No.: 491871-67-1
• Molecular Formula: C13H14FN3
• Molecular Weight: 231.273
• DSSTox Substance ID: DTXSID00459837
• Wikidata: Q82283696
• Mol file: 491871-67-1.mol

Synonyms:491871-67-1;4-(4-FLUOROBENZYLAMINO)-1,2-PHENYLENEDIAMINE;4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine;N4-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine;SCHEMBL1226537;1,2,4-Benzenetriamine, N4-[(4-fluorophenyl)methyl]-;DTXSID00459837;AKOS028114099;AC-28932;FT-0668612

Chemical Property of 4-(4-Fluorobenzylamino)-1,2-phenylenediamine

Chemical Property:

• Vapor Pressure: 1.7E-07mmHg at 25°C
• Boiling Point: 426.9°C at 760 mmHg
• Flash Point: 212°C
• PSA: 64.07000
• Density: 1.296g/cm³
• LogP: 3.83760
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 231.11717562
• Heavy Atom Count: 17
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

4-(4-Fluorobenzylamino)-1,2-phenylenediamine ^*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)F
• Uses: 4-(4-Fluorobenzylamino)-1,2-phenylenediamine is the key intermediate in the synthesis of Retigabine (R189050).

Technology Process of 4-(4-Fluorobenzylamino)-1,2-phenylenediamine

There total 9 articles about 4-(4-Fluorobenzylamino)-1,2-phenylenediamine 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: 100.0%

1-N-[(4-fluorophenyl)methyl]-3-nitrobenzene-1,4-diamine (150812-21-8) → 4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine (491871-67-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃;

DOI:10.1021/acsmedchemlett.8b00315

Reference yield: 43.0%

N4-(3,5-dichloro-2,4,6-trifluorobenzyl)benzene-1,2,4-triamine → 4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine (491871-67-1)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); N-ethyl-N,N-diisopropylamine; In acetonitrile; at 65 ℃; for 61h; Sealed tube; Inert atmosphere; Photolysis;

Reference yield:

2-amino-4-(4-fluorobenzylamino)-nitrobenzene (1263404-74-5) → 4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine (491871-67-1)

Guidance literature:

With hydrogen; 1% Pd/C; In 1,4-dioxane; at 20 - 50 ℃; for 168h;

upstream raw materials:

2-amino-4-(4-fluorobenzylamino)-nitrobenzene

2-nitro-1,4-phenylenediamine

4-fluorobenzaldehyde

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

Downstream raw materials:

retigabine dihydrochloride

tert-butyl 2-(tert-butoxycarbonylimino)-4-(N-para-fluorobenzylimino)aniline formate

diethyl 4-(4-fluorobenzylamino)-1,2-phenylenedicarbamate

C₂₃H₂₈FN₃O₄

Refernces

• 1、 Wang, Lei,Qiao, Guan-Hua,Hu, Hai-Ning,Gao, Zhao-Bing,Nan, Fa-Jun. "Discovery of Novel Retigabine Derivatives as Potent KCNQ4 and KCNQ5 Channel Agonists with Improved Specificity". . p. 27 - 33. Retrieved 2019/01/15.
• 2、 Kumar, Manoj,Reed, Nicholas,Liu, Ruiting,Aizenman, Elias,Wipf, Peter,Tzounopoulos, Thanos. "Synthesis and evaluation of potent KCNQ2/3-specific channel activators". . p. 667 - 677. Retrieved 2016/07/06.