150812-21-8

Basic information

• Product Name: 2-Amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene
• Synonyms: 2-Amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene;N1-(4-fluorobenzyl)-2-nitrobenzene-1,4-diamine;N4-[(4-Fluorophenyl)Methyl]-2-nitro-1,4-benzenediaMine;N-(4-Fluorobenzyl)-3-nitro-p-phenylenediaMine, 98%;N4-(4-Fluoro-benzyl)-2-nitro-benzene-1,4-diaMine;N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diaMine;1,4-BenzenediaMine,N4-[(4-fluorophenyl)Methyl]-2-nitro-;N1-(4-Fluorobenzyl)-3-nitro-1,4-phenylenediamine
• CAS NO: 150812-21-8
• Molecular Formula: C₁₃H₁₂FN₃O₂
• Molecular Weight: 261.255
• EINECS: 1312995-182-4
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 150812-21-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 110.0 to 114.0 °C
• Boiling Point: 436.6 °C at 760 mmHg
• Flash Point: 217.9 °C
• Appearance: Red to brown/Powder
• Density: 1.390
• Vapor Pressure: 7.96E-08mmHg at 25°C
• Refractive Index: 1.681
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: 2.08±0.40(Predicted)
• CAS DataBase Reference: 2-Amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene(150812-21-8)
• EPA Substance Registry System: 2-Amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene(150812-21-8)

Safety Data

• Hazardous Substances Data: 150812-21-8(Hazardous Substances Data)

Usage

Chemical Properties

Red Solid

Uses

Intermediate in the synthesis of Retigabine, a new experimental anticonvulsant drug.

InChI:InChI=1/C13H12FN3O2/c14-10-3-1-9(2-4-10)8-16-11-5-6-12(15)13(7-11)17(18)19/h1-7,16H,8,15H2

Upstream product

• 5307-14-2 2-nitro-1,4-phenylenediamine 
• 459-57-4 4-fluorobenzaldehyde 
• 150812-22-9 2-amino-5-(4-fluorobenzylideneamino)nitrobenzene 

Downstream Products

• 150812-23-0 2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene 

Relevant articles and documents

Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds

A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.

Discovery of Novel Retigabine Derivatives as Potent KCNQ4 and KCNQ5 Channel Agonists with Improved Specificity

Recent research suggests that KCNQ isoforms, particularly the KCNQ4 and KCNQ5 subtypes expressed in smooth muscle cells, are involved in both establishing and maintaining resting membrane potentials and regulating smooth muscle contractility. Retigabine (

(2-AMINO-4(ARYLAMINO)PHENYL) CARBAMATES

A compound, or pharmaceutically acceptable salt thereof, having a formula (I) wherein R1 is H or optionally-substituted alkyl; R2 is optionally-substituted alkyl; R3 and R4 are each independently H or optionally-substituted alkyl; R5 is H, optionally-substituted alkyl, acyl, or alkoxycarbonyl; R6 and R7 are each independently H, deuterium, optionally- substituted alkyl, or R6 and R7 together form a carbocyclic; R8 is optionally-substituted thiazolyl, optionally-substituted thiophenyl, or substituted phenyl, provided that if R8 is 4-halophenyl, then R2 is substituted alkyl or branched alkyl or at least one of R6 or R7 is not H; and R30, R31 and R32 are each independently H, deuterium, halogen, substituted sulfanyl, or optionally-substituted alkoxy.