24613-03-4

Basic information

• Product Name: N-chloroaniline
• Synonyms: N-chloroaniline
• CAS NO: 24613-03-4
• Molecular Formula: C₆H₆ClN
• Molecular Weight: 127.5715
• Mol File: 24613-03-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 70-73 °C
• Boiling Point: 173 °C at 760 mmHg
• Flash Point: 58.4 °C
• Appearance: /
• Density: 1.229 g/cm³
• PKA: -0.35±0.38(Predicted)
• CAS DataBase Reference: N-chloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-chloroaniline(24613-03-4)
• EPA Substance Registry System: N-chloroaniline(24613-03-4)

Safety Data

• Hazardous Substances Data: 24613-03-4(Hazardous Substances Data)

Usage

General Description

N-chloroaniline is an organic chemical compound that is a derivative of aniline, with a chlorine atom substitution at the nitrogen atom. It is a pale yellow to brown solid at room temperature and is mainly used as an intermediate in the synthesis of various industrial chemicals and dyes. N-chloroaniline is also used in the production of pharmaceuticals, pesticides, and corrosion inhibitors. It is a reactive compound that can undergo chemical reactions such as chlorination, diazotization, and nitration. N-chloroaniline is considered to be toxic and harmful if ingested, inhaled, or comes into contact with the skin, and it is classified as a hazardous substance with potential environmental impacts if not handled and disposed of properly.

Upstream product

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

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 articles and documents

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 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.

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.