4-Acetamido-3-ethoxynitrobenzene

Base Information

• Chemical Name: 4-Acetamido-3-ethoxynitrobenzene
• CAS No.: 116496-76-5
• Molecular Formula: C10H12N2O4
• Molecular Weight: 224.216
• Hs Code.: 2924299090
• European Community (EC) Number: 601-432-8
• DSSTox Substance ID: DTXSID60387001
• Nikkaji Number: J60.149G
• Wikidata: Q82180852
• Mol file: 116496-76-5.mol

Synonyms:ACE-011;sotatercept

Chemical Property of 4-Acetamido-3-ethoxynitrobenzene

Chemical Property:

• Vapor Pressure: 3.9E-07mmHg at 25°C
• Melting Point: 164-165 °C
• Refractive Index: 1.582
• Boiling Point: 416.2 °C at 760 mmHg
• PKA: 13.32±0.70(Predicted)
• Flash Point: 205.5 °C
• PSA: 84.15000
• Density: 1.282 g/cm³
• LogP: 2.54810
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 224.07970687
• Heavy Atom Count: 16
• Complexity: 264

Purity/Quality:

98%min ^*data from raw suppliers

4-Acetamido-3-ethoxynitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)C
• Recent EU Clinical Trials: A Phase 3, Randomized, Double-blind, Placebo-controlled Study to Evaluate Sotatercept When Added to Background Pulmonary Arterial Hypertension

Technology Process of 4-Acetamido-3-ethoxynitrobenzene

There total 7 articles about 4-Acetamido-3-ethoxynitrobenzene 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: 98.0%

ethyl bromide (74-96-4) + N-(2-hydroxy-4-nitrophenyl)acetamide (25351-89-7) → 4-acetamido-3-ethoxynitrobenzene (116496-76-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1021/jm040159c

Reference yield:

5-Nitro-2-aminophenol (121-88-0) → 4-acetamido-3-ethoxynitrobenzene (116496-76-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / AcOH / 60 °C

2: 98 percent / K₂CO₃ / dimethylformamide / 60 °C

With potassium carbonate; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm040159c

Reference yield:

2'-ethoxyacetanilide (581-08-8) → 4-acetamido-3-ethoxynitrobenzene (116496-76-5)

Guidance literature:

With nitric acid; at 25 - 40 ℃;

upstream raw materials:

2'-ethoxyacetanilide

nitric acid

acetic acid

acetic anhydride

Downstream raw materials:

N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide

6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile

N-(4-[3-chloro-4-(pyridin-2-ylmethoxy)phenylamino]-3-cyano-7-ethoxyquinoline-6-yl)acetamide

3-chloro-N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide

Refernces

• 1、 Carmi, Caterina,Galvani, Elena,Vacondio, Federica,Rivara, Silvia,Lodola, Alessio,Russo, Simonetta,Aiello, Stefania,Bordi, Fabrizio,Costantino, Gabriele,Cavazzoni, Andrea,Alfieri, Roberta R.,Ardizzoni, Andrea,Petronini, Pier Giorgio,Mor, Marco. "Irreversible inhibition of epidermal growth factor receptor activity by 3-aminopropanamides". scheme or table. p. 2251 - 2264. Retrieved 2012/05/20.
• 2、 Tsou, Hwei-Ru,Overbeek-Klumpers, Elsebe G.,Hallett, William A.,Reich, Marvin F.,Floyd, M. Brawner,Johnson, Bernard D.,Michalak, Ronald S.,Nilakantan, Ramaswamy,Discafani, Carolyn,Golas, Jonathan,Rabindran, Sridhar K.,Shen, Ru,Shi, Xiaoqing,Wang, Yu-Fen,Upeslacis, Janis,Wissner, Allan. "Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity". . p. 1107 - 1131. Retrieved 2007/10/03.