N-(2-bromo-4-nitrophenyl)acetamide

Base Information

• Chemical Name: N-(2-bromo-4-nitrophenyl)acetamide
• CAS No.: 57045-86-0
• Molecular Formula: C8H7BrN2O3
• Molecular Weight: 259.059
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID00462008
• Nikkaji Number: J2.645.186H
• Wikidata: Q82286473
• Mol file: 57045-86-0.mol

Synonyms:N-(2-bromo-4-nitrophenyl)acetamide;57045-86-0;N-Acetyl 2-bromo-4-nitroaniline;N-Acetyl2-bromo-4-nitroaniline;N-(2-bromo-4-nitro-phenyl)-acetamide;MFCD00569284;SCHEMBL5455180;n-acetyl-2-bromo-4-nitroaniline;DTXSID00462008;CVRYGNVWNQYYEC-UHFFFAOYSA-N;AKOS002952550;SY288516;CS-0136799;E79644;A869776

Chemical Property of N-(2-bromo-4-nitrophenyl)acetamide

Chemical Property:

• Refractive Index: 1.5190 (estimate)
• PSA: 74.92000
• Density: 1.8233 (rough estimate)
• LogP: 2.91190
• Storage Temp.: 2-8°C
• Water Solubility.: 17.7g/L(room temperature)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 257.96400
• Heavy Atom Count: 14
• Complexity: 241

Purity/Quality:

98%Min ^*data from raw suppliers

N-Acetyl2-bromo-4-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])Br
• Uses: N-Acetyl 2-bromo-4-nitroaniline is used in the preparation of pyridine-fused perylene imides. In addition it is used in the synthesis of catbazoles using hypervalent iodine oxidant.

Technology Process of N-(2-bromo-4-nitrophenyl)acetamide

There total 10 articles about N-(2-bromo-4-nitrophenyl)acetamide 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: 88.0%

2-bromo-4-nitroaniline (13296-94-1) + acetic anhydride (108-24-7) → N-(2-bromo-4-nitro-phenyl)-acetamide (57045-86-0)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane;

DOI:10.1021/ol0270982

Reference yield: 72.0%

N-(4-Nitrophenyl)acetamide (104-04-1) → N-(2-bromo-4-nitro-phenyl)-acetamide (57045-86-0)

Guidance literature:

With N-Bromosuccinimide; palladium diacetate; copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.6b02731

Reference yield: 30.0%

N-acetyl-2-bromoaniline (614-76-6) → N-(2-bromo-6-nitro-phenyl)-acetamide (245115-83-7) + N-(2-bromo-4-nitro-phenyl)-acetamide (57045-86-0)

Guidance literature:

With sulfuric acid; nitric acid; at 20 ℃; for 7h;

DOI:10.1021/ol048806h

upstream raw materials:

N-acetyl-2-bromoaniline

acetic acid-(N-bromo-4-nitro-anilide)

2-bromo-4-nitroaniline

acetic anhydride

Downstream raw materials:

2-methyl-6-nitrobenzothiazole

N,N’-bis(1-ethylpropyl)-2-(4-nitroacetanilide-2-yl)perylene-3,4:9,10-tetracarboxylic acid bisimide

N-(5-nitro-[1,1'-biphenyl]-2-yl)acetamide

2-propyl-5-nitrobenzoimidazole

Refernces

• 1、 Li, Ze-lin,Sun, Kang-kang,Cai, Chun. "Cobalt(II)-catalyzed regioselective C-H halogenation of anilides". supporting information. p. 5433 - 5440. Retrieved 2018/08/12.
• 2、 Das, Riki,Kapur, Manmohan. "Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides". . p. 1114 - 1126. Retrieved 2018/06/18.