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

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

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

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

Downstream Products

• 13296-94-1 2-bromo-4-nitroaniline 
• 436090-22-1 N-(4-amino-2-bromophenyl)acetamide 
• 488082-69-5 3-(2-acetylamino-5-ethynyl-phenylethynyl)-5-ethynyl-benzoic acid methyl ester 
• 488082-57-1 2-bromo-4-[3,3-diethyl-1-triazenyl]-N-acetylaniline 
• 488082-64-0 C₁₄H₁₈N₄O 
• 488082-58-2 C₁₇H₂₆N₄OSi 
• 488082-67-3 3-(2-acetylamino-5-iodo-phenylethynyl)-5-iodo-benzoic acid methyl ester 
• 488082-61-7 2-(2-acetylamino-5-iodo-phenylethynyl)-4-iodo-benzoic acid methyl ester 
• 488082-60-6 C₂₆H₃₃N₇O₃ 
• 488082-66-2 C₂₆H₃₃N₇O₃ 
• 848047-41-6 N-(2-bromo-4-nitrophenyl)-N-(2-methyl-2-propenyl)acetamide 
• 1792-40-1 2-methyl-5-nitrobenzimidazole 
• 5805-43-6 2-propyl-5-nitrobenzoimidazole 
• 68612-69-1 N-(5-nitro-[1,1'-biphenyl]-2-yl)acetamide 

Relevant articles and documents

Cobalt(II)-catalyzed regioselective C-H halogenation of anilides

A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.

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.

Discovery of wtRET and V804MRET Inhibitors: From Hit to Lead

Oncogenic activation of RET kinase has been found in several neoplastic diseases, like medullary thyroid carcinoma, multiple endocrine neoplasia, papillary thyroid carcinoma, and non-small-cell lung cancer. Currently approved RET inhibitors were not originally designed to be RET inhibitors, and their potency against RET kinase has not been optimized. Hence, novel compounds able to inhibit both wild-type RET (wtRET) and its mutants (e.g., V804MRET) are needed. Herein we present the development and the preliminary evaluation of a new sub-micromolar wtRET/V804MRET inhibitor, N-(2-fluoro-5-trifluoromethylphenyl)-N′-{4′-[(2′′-benzamido)pyridin-4′′-ylamino]phenyl}urea (69), endowed with a 4-anilinopyridine structure, starting from our previously identified 4-anilinopyrimidine hit compound. Profiling against a panel of kinases indicated 69 as a multi cKIT/wtRET/V804MRET inhibitor.

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.

Highly effective Pd-catalyzed ortho olefination of acetanilides: Broad substrate scope and high tolerability

Bring it on! An effective Pd-catalyzed ortho olefination of various acetanilides has been developed. This transformation has a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of acetanilide substrates, providing a straightforward access to highly functionalized arenes.

SUBSTITUTED BICYCLIC QUINAZOLIN-4-YLAMINE DERIVATIVES

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Copper-Mediated Cross-Coupling Reactions of N-Unsubstituted Sulfoximines and Aryl Halides

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Hydrogen Bond-Stabilized Helix Formation of a m-Phenylene Ethynylene Oligomer

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Oxidative Bromination of Aromatic Amides using Sodium Perborate as Oxidant

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