57045-86-0

Basic information

• Product Name: N-Acetyl2-bromo-4-nitroaniline
• Synonyms: N-Acetyl2-bromo-4-nitroaniline;1-acetamido-2-bromo-4-nitrobenzene
• CAS NO: 57045-86-0
• Molecular Formula: C₈H₇BrN₂O₃
• Molecular Weight: 259.058
• Mol File: 57045-86-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.8233 (rough estimate)
• Refractive Index: 1.5190 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 17.7g/L(room temperature)
• CAS DataBase Reference: N-Acetyl2-bromo-4-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl2-bromo-4-nitroaniline(57045-86-0)
• EPA Substance Registry System: N-Acetyl2-bromo-4-nitroaniline(57045-86-0)

Safety Data

• Hazardous Substances Data: 57045-86-0(Hazardous Substances Data)

Usage

Description

N-Acetyl2-bromo-4-nitroaniline is an organic compound that serves as an important intermediate in the synthesis of various chemical compounds.

Uses

Used in Organic Synthesis:
N-Acetyl2-bromo-4-nitroaniline is used as a key intermediate in the preparation of pyridine-fused perylene imides, which are a class of organic dyes with potential applications in optoelectronic devices and materials science.
Used in Synthesis of Catbazoles:
N-Acetyl2-bromo-4-nitroaniline is also utilized in the synthesis of catbazoles, a group of organic compounds with potential applications in pharmaceutical and chemical research. The synthesis process involves the use of hypervalent iodine oxidant, which facilitates the formation of the desired catbazole products.

Upstream product

• 10403-47-1 2-bromo 5-nitroaniline 
• 100-01-6 4-nitro-aniline 
• 615-36-1 2-bromoaniline 
• 614-76-6 N-acetyl-2-bromoaniline 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 13296-94-1 2-bromo-4-nitroaniline 
• 108-24-7 acetic anhydride 
• 3054-89-5 acetic acid-(N-bromo-4-nitro-anilide) 
• 75-36-5 acetyl chloride 

Downstream Products

• 1792-40-1 2-methyl-5-nitrobenzimidazole 
• 5805-43-6 2-propyl-5-nitrobenzoimidazole 
• 2941-63-1 2-methyl-6-nitrobenzothiazole 
• 1440762-46-8 N,N’-bis(1-ethylpropyl)-2-(4-nitroacetanilide-2-yl)perylene-3,4:9,10-tetracarboxylic acid bisimide 
• 848047-41-6 N-(2-bromo-4-nitrophenyl)-N-(2-methyl-2-propenyl)acetamide 
• 488082-66-2 C₂₆H₃₃N₇O₃ 
• 488082-60-6 C₂₆H₃₃N₇O₃ 
• 488082-61-7 2-(2-acetylamino-5-iodo-phenylethynyl)-4-iodo-benzoic acid methyl ester 
• 488082-67-3 3-(2-acetylamino-5-iodo-phenylethynyl)-5-iodo-benzoic acid methyl ester 
• 488082-58-2 C₁₇H₂₆N₄OSi 
• 488082-64-0 C₁₄H₁₈N₄O 
• 488082-57-1 2-bromo-4-[3,3-diethyl-1-triazenyl]-N-acetylaniline 
• 488082-69-5 3-(2-acetylamino-5-ethynyl-phenylethynyl)-5-ethynyl-benzoic acid methyl ester 
• 436090-22-1 N-(4-amino-2-bromophenyl)acetamide 

Relevant articles and documents

1,3,3-Trimethylindolin-5-amine and 4-Formylphenyl 4,4-Dimethylchroman-6-carboxylate Thiosemicarbazone (OHet72)

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Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis

Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.