57045-85-9

Usage

Uses

Used in Pharmaceutical Industry:
2'-BROMO-4'-CHLOROACETANILIDE is used as a reagent in the palladium-catalyzed direct arylation with 2-bromoacetanilides. This reaction is a key step in the synthesis of N-Acetyl 2-bromo-4-chloroaniline, which is an important intermediate in the production of various pharmaceuticals.
Used in Agrochemical Industry:
2'-BROMO-4'-CHLOROACETANILIDE is also utilized in the synthesis of agrochemicals, specifically as a precursor for the production of herbicides and insecticides. Its unique chemical properties allow for the development of effective and targeted agrochemicals.

InChI:InChI=1/C8H7BrClNO/c1-5(12)11-8-3-2-6(10)4-7(8)9/h2-4H,1H3,(H,11,12)

Upstream product

• 1439-13-0 N-bromo-4-chloroacetanilide 
• 114233-33-9 N-(2-bromo-4-chloro-phenyl)-malonamic acid 
• 29551-80-2 acetic acid-(2-bromo-N-chloro-anilide) 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 873-38-1 4-chloro-2-bromoaniline 
• 108-24-7 acetic anhydride 
• 103-84-4 Acetanilid 
• 106-47-8 4-chloro-aniline 
• 67-64-1 acetone 
• 123-54-6 acetylacetone 

Downstream Products

• 827-25-8 2-bromo-4-chloro-6-nitrobenzenamine 
• 873-38-1 4-chloro-2-bromoaniline 
• 123028-19-3 N-acetyl-2-pentyn-1-yl-4-chloroaniline 
• 123028-22-8 N-(4-chloro-2-(phenylethynyl)phenyl)acetamide 
• 123028-21-7 4-chloro-2-(1-hexynyl)-N-ethanoylaniline 
• 123028-20-6 N-acetyl-2-(3-methylbutyn-1-yl)-4-chloroaniline 
• 123028-39-7 N-acetyl-2-n-butyl-5-chloroindole 
• 123028-41-1 1-(5-chloro-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 79044-04-5 N-(4-Chloro-2-vinyl-phenyl)-acetamide 
• 1356388-76-5 2-(2-acetamido-5-chlorophenyl)pyridine 1-oxide 
• 1423161-88-9 4-chloro-2-(1-methyl-1H-pyrazol-5-yl)aniline 
• 7148-08-5 N-(5-chloro-[1,1'-biphenyl]-2-yl)acetamide 
• 41192-33-0 5-chloro-1-methylindolin-2-one 

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.

An organocatalytic C-C bond cleavage approach: A metal-free and peroxide-free facile method for the synthesis of amide derivatives

A facile organocatalytic approach has been devised towards the synthesis of amide derivatives using 1,3-dicarbonyls as easily available acyl-sources under peroxide-free reaction conditions. This transformation was accomplished by the cleavage of the C-C bond in the presence of TEMPO as an organocatalyst and excludes the use of transition-metals and harsh reaction conditions. A broad range of substrates with diverse functional groups were well tolerated and delivered the products in high yields.

Method for synthesizing N-phenylacetamide compounds

The present invention provides a method for synthesizing N-phenylacetamide compounds. The synthesis method takes an azide terminal olefin compound represented by a formula (I) as a raw material, sodium trifluoromethanesulfonate as an additive, potassium persulfate as an oxidant, and acetonitrile as a solvent, and a reaction is carried out at 80 DEG C for 5 hours, so that a corresponding target product is obtained. The synthesis method of the invention has the characteristics of small environmental hazard, mild reaction conditions, simple operation and the like.

Copper-Catalyzed Site-Selective Oxidative C?C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol

A copper-catalyzed approach for the N-acylation of anilines with acetone and acetophenones via C?C bond cleavage is described. Under the developed conditions both CHCl3 and CH2Cl2 were identified as potential C1-source to promote the transformation. The reaction features a site selective C?C bond cleavage to install the amide moieties with high functional-group compatibility and wide substrate scope. The developed method avoids the use of sensitive and narcotic agents. The method also represents an excellent complement to the previous protocols with lower E-factor (13.91 mg/1 mg) than current industrially used method (E-factor 17.54 mg/1 mg). The developed approach has also been extended for the effective preparation of pyridine derivatives and paracetamol in gram scale. The course of the reaction was monitored by 1H NMR as a preliminary investigation of the reaction mechanism. (Figure presented.).

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.

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.

Regioselective and efficient bromination of anilides on water using HBr and Selectfluor

A metal-, additive-, and Br2-free highly regioselective bromination of anilides using HBr and Selectfluor is presented. This reaction proceeded under mild conditions with high efficiency and good functional group tolerance, and water served as the solvent. In general, with substrates bearing no para-substituent, para-mono-bromination occurred exclusively, while ortho-mono-brominated anilides were the only products when para-positions were blocked. The incorporation of a stronger orienting group might result in a reversed regioselectivity, and the reaction was sensitive to steric hindrance.

CARBOXAMIDE DERIVATIVES

The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt or co-crystal thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.