57045-85-9

Basic information

• Product Name: 2'-BROMO-4'-CHLOROACETANILIDE
• Synonyms: 2'-Bromo-4'-chloro-N-phenylacetamide;N-Acetyl 2-bromo-4-chloroaniline;acetamide, N-(2-bromo-4-chlorophenyl)-;N-(2-bromo-4-chlorophenyl)acetamide(SALTDATA: FREE);N-(2-bromo-4-chloro-phenyl)ethanamide;N-(2-BROMO-4-CHLOROPHENYL)ACETAMIDE;2-BROMO-4-CHLORO ACETANILIDE;2'-BROMO-4'-CHLOROACETANILIDE
• CAS NO: 57045-85-9
• Molecular Formula: C₈H₇BrClNO
• Molecular Weight: 248.5
• Product Categories: Anilines, Amides & Amines;Bromine Compounds;Chlorine Compounds
• Mol File: 57045-85-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 136 °C(Solv: ethanol (64-17-5))
• Boiling Point: 370.7 °C at 760 mmHg
• Flash Point: 178 °C
• Appearance: /
• Density: 1.649 g/cm³
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• PKA: 13.32±0.70(Predicted)
• CAS DataBase Reference: 2'-BROMO-4'-CHLOROACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-BROMO-4'-CHLOROACETANILIDE(57045-85-9)
• EPA Substance Registry System: 2'-BROMO-4'-CHLOROACETANILIDE(57045-85-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 57045-85-9(Hazardous Substances Data)

Usage

Description

2'-BROMO-4'-CHLOROACETANILIDE is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is characterized by the presence of a bromo and chloro substituent on the aromatic ring, which imparts unique chemical properties and reactivity to the molecule.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.).