Related Experiment Video

Updated: May 18, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

(Z)-3-Meth-oxy-N-[(5-nitro-thio-phen-2-yl)methyl-idene]aniline

Tufan Akbal, Erbil Ağar, Ahmet Erdönmez

    Acta Crystallographica. Section E, Structure Reports Online
    |September 13, 2012
    PubMed

    More Related Videos

    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones07:30

    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

    Published on: January 21, 2020

    Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones10:17

    Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

    Published on: February 7, 2019

    Related Concept Videos

    Diazonium Group Substitution: –OH and –H01:19

    Diazonium Group Substitution: –OH and –H

    Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
    Nomenclature of Aryl and Heterocyclic Amines01:10

    Nomenclature of Aryl and Heterocyclic Amines

    The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
    ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

    ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

    All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
    Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

    Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

    Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
    Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

    Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

    Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
    In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
    2° Amines to N-Nitrosamines: Reaction with NaNO201:20

    2° Amines to N-Nitrosamines: Reaction with NaNO2

    Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.