614-83-5

Usage

Uses

Used in Pharmaceutical Synthesis:
2'-Bromo-4'-methylacetanilide is utilized as an intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs. Its chemical structure allows for the creation of a wide range of biologically active compounds, making it a valuable building block in medicinal chemistry.
Used in Organic Chemistry Reactions:
As a reagent, 2'-bromo-4'-methylacetanilide is employed in various organic chemistry reactions, facilitating the synthesis of complex organic molecules. Its presence can influence the reaction pathways and outcomes, contributing to the advancement of chemical research.
Used in Medicinal Chemistry Research:
2'-Bromo-4'-methylacetanilide may have applications in the field of medicinal chemistry, where it can be used to study the interactions between biological molecules and potential drug candidates. Its unique structure can provide insights into the design and optimization of new therapeutic agents.
Used in Biochemistry Studies:
In biochemistry, 2'-bromo-4'-methylacetanilide can be used to investigate the mechanisms of enzymatic reactions and the binding properties of biomolecules. Its presence can help researchers understand the fundamental processes that govern biological systems and aid in the development of targeted therapies.
Overall, 2'-bromo-4'-methylacetanilide is a versatile chemical compound with applications spanning across pharmaceutical synthesis, organic chemistry reactions, medicinal chemistry research, and biochemistry studies. Its unique properties and potential uses make it an important tool in the advancement of scientific knowledge and the development of novel therapeutic agents.

InChI:InChI=1/C9H10BrNO/c1-6-3-4-9(8(10)5-6)11-7(2)12/h3-5H,1-2H3,(H,11,12)

Upstream product

• 99847-72-0 acetic acid-(N-bromo-p-toluidide) 
• 103-89-9 4-Methylacetanilide 
• 583-68-6 2-bromo-p-toluidine 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 106-49-0 p-toluidine 

Downstream Products

• 68882-99-5 2-ethenyl-4-methylacetanilide 
• 6968-24-7 2,6-Dibromo-4-methylaniline 
• 106-49-0 p-toluidine 
• 52488-28-5 1-bromo-3-methyl-5-nitrobenzene 
• 42860-02-6 3‐bromo‐5‐chlorobenzoic acid 
• 101421-16-3 3-bromo-4-chloro-2,6-dinitro-toluene 
• 21900-27-6 3-bromo-5-chlorobenzoic acid chloride 
• 329944-72-1 1-bromo-3-chloro-5-methylbenzene 
• 22603-57-2 6-chloro-3-methyl-2,4-dinitro-aniline 
• 99514-30-4 (6-chloro-3-methyl-2,4-dinitro-phenyl)-phenyl ether 
• 107682-13-3 (6-chloro-3-methyl-2,4-dinitro-phenyl)-p-tolyl-amine 
• 190903-72-1 N-[2-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-methylphenyl]acetamide 
• 959855-49-3 1-(4-methoxyphenyl)-2,6-dimethyl-1H-benzimidazole 
• 2941-71-1 2,6-dimethylbenzothiazole 

Relevant academic research and scientific papers

Nickel(II)- And Silver(I)-Catalyzed C-H Bond Halogenation of Anilides and Carbamates

ortho -C-H bond halogenation of anilides and N -aryl carbamates using easily available N -halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds.

Site-Specific Synthesis of Carbazole Derivatives through Aryl Homocoupling and Amination

We synthesized various carbazoles from anilines through a three-step process with good overall yields (up to 48percent). This process comprises N -acetylation, copper(0)-mediated Ullmann homocoupling, and acid-mediated intramolecular amination. It permits various functional groups on the substrate. Scale-up of the developed three-step synthetic route to carbazoles was also demonstrated.

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

We developed a mild aromatic halogenation reaction using a combination of N-halosuccinimide and PhSSiMe3 or PhSSPh. Less reactive aromatic compounds, such as methyl 4-methoxybenzoate, were brominated with PhSSiMe3 or PhSSPh and N-bromosuccinimide in high yields. No reaction was observed in the absence of PhSSiMe3 or PhSSPh. This method is also applicable to chlorination reactions using N-chlorosuccinimide and PhSSPh.

A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst

A simple and practical heterogeneous Cu-MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu-MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N-halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.

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.

Combining Eosin y with Selectfluor: A Regioselective Brominating System for Para-Bromination of Aniline Derivatives

A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.

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.

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.

Synthesis of 2-methylbenzoxazoles directly from: N -phenylacetamides catalyzed by palladium acetate

A method to synthesize 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by Pd(OAc)2 in the presence of K2S2O8 and TfOH has been developed. The desired products were obtained in moderate to excellent yields. This approach provides a facile procedure to prepare benzoxazoles with available substrates. It is found that TfOH is the key factor for this cyclization reaction. A plausible mechanism of the reaction is proposed according to the control reactions and the literature.

Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert -Butyl Hydroperoxide

A novel tert -butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.