24613-03-4

Usage

Uses

Used in Chemical Synthesis:
N-chloroaniline is utilized as an intermediate in the synthesis of a variety of industrial chemicals and dyes, contributing to the production of a wide range of colorants and other chemical products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-chloroaniline serves as a key intermediate, playing a crucial role in the development and manufacturing of certain medications.
Used in Pesticide Formulation:
N-chloroaniline is employed in the formulation of pesticides, where it contributes to the creation of compounds designed to control, repel, or kill pests.
Used in Corrosion Inhibition:
As a component in corrosion inhibitors, N-chloroaniline helps to protect materials from the damaging effects of corrosion, extending the service life of various industrial equipment and structures.
Given the hazardous nature of N-chloroaniline, it is imperative that its applications are managed with strict adherence to safety protocols to ensure minimal environmental and health risks.

Upstream product

• 62-53-3 aniline 
• 60-29-7 diethyl ether 
• 624-85-1 ethyl hypochlorite 

Downstream Products

• 106-47-8 4-chloro-aniline 
• 95-51-2 o-chloroaniline 
• 1227476-15-4 Azobenzene 
• 93-98-1 N-phenyl benzoyl amide 

Relevant academic research and scientific papers

Two-step continuous flow synthesis of amide via oxidative amidation of methylarene

A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.

Copper-catalyzed one-pot oxidative amidation between methylarenes and amines

A new method for the direct one-pot oxidative amidation between methylarenes and amines catalyzed by copper has been developed. This method integrates methylarene oxidation and amide bond formation, which are usually accomplished separately, into a single operation. In addition, the reaction provides a relatively high yield and has a wide substrate scope. Moreover, the starting reagents are abundant and available in a convenient way at a cheaper price.

Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C-H activation

A one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, was developed. This cross-coupling reaction integrates alcohol oxidation and amide bond formation, which are usually accomplished separately, into a single operation. And it was green, simple and convenient, which has a wide substrate scope and makes use of cheap, abundant, and easily available reagents. The practical value of this method is highlighted through the synthesis of a high-profile pharmaceutical agent, acetylprocainamide.

Hydrogenation of halogen-substituted aromatic nitro compounds

This invention relates to the hydrogenation of halogen-substituted aromatic nitro compounds and in particular provides a novel catalyst for use in such processes. In more detail a catalyst suitable for use in the hydrogenation of halogen-substituted aromatic nitro compounds substantially without simultaneous dehalogenation comprises one or more metals from the group consisting of platinum, palladium, rhodium, iridium, ruthenium and osmium supported on or impregnated into a carrier material comprising carbon activated with phosphoric acid or a salt thereof.

Synthesis of indoles from anilines and intermediates therein

Preparing indoles and intermediates therefor by reacting an N-haloaniline with a β-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the β-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an α-ethyl-β -carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures. The thio-ether-indole and thio-ether indolenine derivatives are useful as intermediates to make the indoles without the thio-ether group. The indoles are known compounds having a wide variety of uses, e.g., in making perfumes, dyes, amino acids, pharmaceuticals, agricultural chemicals and the like.

Preparation of esters of phosphorus acids

Esters of phosphorus acids are prepared by an improved process whereby aromatic alcohols and phosphorus halides are reacted at specified temperatures in the presence of amine catalysts thereby providing high yields of substantially pure esters and allowing preparation of selected halogen-containing mono- and di-esters of phosphorus acids wherein halogen is directly bonded to phosphorus having substantially no side reactant contamination. The phosphorus esters are useful as intermediates in the preparation of plasticizers, oil additives and functional fluids.

Synthesis of oxindoles from anilines and β-thio carboxylic esters or amides

Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with β-thio esters or β-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho-[thio-ether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thio-ether (aminocarbonyl) alkyl]aniline, reacting the orthosubstituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.