6270-07-1

Basic information

• Product Name: N-ACETYL-2-(4-NITROPHENYL)ETHYLAMINE
• Synonyms: N-ACETYL-4-NITROPHENETHYLAMINE;N-ACETYL-2-(4-NITROPHENYL)ETHYLAMINE;N-[2-(4-NITROPHENYL)ETHYL]ACETAMIDE;n-(2-(p-nitrophenyl)ethyl)acetamide;n-[2-(4-nitrophenyl)ethyl]-acetamid;Acetylnitrophenylethylamine;N-(4-NITROPHENETHYL)ACETAMIDE;N-(4-NITROPHENYLETHYL)ACETAMID
• CAS NO: 6270-07-1
• Molecular Formula: C₁₀H₁₂N₂O₃
• Molecular Weight: 208.21
• Mol File: 6270-07-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 140°C
• Boiling Point: 451.4 °C at 760 mmHg
• Flash Point: 226.8 °C
• Appearance: /
• Density: 1.203 g/cm³
• Vapor Pressure: 2.43E-08mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-ACETYL-2-(4-NITROPHENYL)ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-2-(4-NITROPHENYL)ETHYLAMINE(6270-07-1)
• EPA Substance Registry System: N-ACETYL-2-(4-NITROPHENYL)ETHYLAMINE(6270-07-1)

Safety Data

• Hazardous Substances Data: 6270-07-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow powder

Uses

N-ACETYL-2-(4-NITROPHENYL)ETHYLAMINE can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

450Kg of concentrated sulfuric acid was added to the reactor, the temperature of the reaction solution was room temperature, the reaction solution containing the intermediate 1 was slowly added dropwise, and after sufficient stirring, 75 kg of 70% nitric acid was slowly added. After stirring until completion of the reaction, 800kg of crushed ice was added to the reaction solution and stirred constantly , Finally, pH was adjusted to 7~8 with ammonia solution to give crude product after filtration, crude product was recrystallized from methyl ethyl ketone to give 140 Kg of Intermediate 2, with a yield of 81.5%.

InChI:InChI=1/C10H12N2O3/c1-8(13)11-7-6-9-2-4-10(5-3-9)12(14)15/h2-5H,6-7H2,1H3,(H,11,13)

Upstream product

• 64-04-0 phenethylamine 
• 3240-95-7 N-benzylidene-2-phenylethanamine 
• 877-95-2 methyl-N-(benzyl-methyl)-formamide 
• 7697-37-2 nitric acid 
• 24954-67-4 2-(p-nitrophenyl)ethylamine 
• 108-24-7 acetic anhydride 

Downstream Products

• 159417-92-2 4-<2-(acetamido)ethyl>-acetanilide 
• 248599-61-3 N-[2-(p-nitrophenoxy)ethyl]-N-[2-(p-nitrophenoxy)ethyl]-p-nitrophenethylamine 
• 226992-23-0 N-(p-chlorobenzyl)-N-[2-(p-nitrophenoxy)ethyl]-p-nitrophenethylamine 
• 446877-73-2 N-benzoyl-N-[2-(naphth-1-yl-oxy)ethyl]-p-nitrophenethylamine 
• 446877-50-5 N-benzoyl-N-[2-(p-nitrophenoxy)ethyl]-p-nitrophenethylamine 
• 446877-75-4 N-benzoyl-N-[2-(naphth-1-yl-oxy)ethyl]-p-(amino)phenethylamine 
• 446877-70-9 N-benzyl-N-[2-(naphth-1-yl-oxy)ethyl]-p-nitrophenethylamine 
• 226992-26-3 C₂₃H₂₆ClN₃O 
• 446877-74-3 N-benzyl-N-[2-(naphth-1-yl-oxy)ethyl]-p-(amino)phenethylamine 
• 226992-14-9 N-benzyl-N-[2-(p-nitrophenoxy)ethyl]-p-nitrophenethylamine 
• 176447-94-2 [Cy₃B]-N-Demethyldofetilide 

Relevant articles and documents

PYRAZOLOPYRIMIDINE DERIVATIVES, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR USE IN PREVENTING OR TREATING CANCER, AUTOIMMUNE DISEASE AND BRAIN DISEASE CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a pyrazolopyrimidine derivative, a preparation method thereof and a pharmaceutical composition comprising the same as an active ingredient for the prevention or treatment of cancer, autoimmune disease and brain disease. The pyrazolopyrimidine derivative of the present invention exhibits excellent Bruton's tyrosine kinase inhibition activity, so that it can be effectively used as a pharmaceutical composition for the prevention or treatment of cancer, autoimmune disease and Parkinson's disease.

New p-methylsulfonamido phenylethylamine analogues as class III antiarrhythmic agents: Design, synthesis, biological assay, and 3D-QSAR analysis

Class III antiarrhythmic agents selectively delay the effective refractory period (ERP) and increase the transmembrance action potential duration (APD). Using dofetilide (2) as a template of class III antiarrhythmic agents, we designed and synthesized 16 methylsulfonamido phenylethylamine analogues (4a-d and 5a-1). Pharmacological assay indicated that all of these compounds showed activity for increasing the ERP in isolated animal atrium; among them, the effective concentration of compound 4a is 1.6 × 10-8 mol/L in increasing ERP by 10 ms, slightly less potent than that of 2, 1.1 × 10-8 mol/L. Compound 4a also produced a slightly lower change in ERP at 10-5 M, ΔERP% = 17.5% (ΔERP% = 24.0% for dofetilide). On the basis of this bioassay result, these 16 compounds together with dofetilide were investigated by the three-dimensional quantitative structure-activity relationship (3D-QSAR) techniques of comparative molecular field analysis (CoMFA), comparative molecular similarity index analysis (CoMSIA), and the hologram QSAR (HQSAR). The 3D-QSAR models were tested with another 11 compounds (4e-h and 5m-s) that we synthesized later. Results revealed that the CoMFA, CoMSIA, and HQSAR predicted activities for the 11 newly synthesized compounds that have a good correlation with their experimental value, r2 = 0.943, 0.891, and 0.809 for the three QSAR models, respectively. This indicates that the 3D-QSAR models proved a good predictive ability and could describe the steric, electrostatic, and hydrophobic requirements for recognition forces of the receptor site. On the basis of these results, we designed and synthesized another eight new analogues of methanesulfonamido phenylethyamine (6a-h) according to the clues provided by the 3D-QSAR analyses. Pharmacological assay indicated that the effective concentrations of delaying the ERP by 10 ms of these newly designed compounds correlated well with the 3D-QSAR predicted values. It is remarkable that the percent change of delaying ERP at 10-5 M compound 6c is much higher than that of dofetilide; the effective concentration of compound 6c is 5.0 × 10-8mol/L in increasing the ERP by 10 ms, which is slightly lower than that of 2. The results showed that the 3D-QSAR models are reliable and can be extended to design new antiarrhythmic agents.