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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
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.
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...
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...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.

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Related Experiment Video

Updated: Jul 16, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Synthesis, Structure and Performance of an Insensitive Diazonium Inner Salt Energetic Material.

Haifeng Wang1, Jinxin Wang1,2, Ruibing Lv1

  • 1National Key Laboratory of Chemical Explosion Safety, Institute of Chemical Materials, China Academy of Engineering Physics (CAEP), Mianyang 621900, China.

Molecules (Basel, Switzerland)
|July 15, 2026
PubMed
Summary

A new energetic material, 2-nitro-5-oxo[1,2,4]triazolo[1,5-c]pyrimidin-8-diazonium-7-olate (NTPD), was synthesized. This novel compound shows high thermal stability and low mechanical sensitivity, making it a safer energetic material.

Keywords:
diazoniumenergetic materialsfused-ringinner salt

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Last Updated: Jul 16, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups
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Molten-Salt Synthesis of Complex Metal Oxide Nanoparticles
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Area of Science:

  • Energetic Materials Science
  • Organic Synthesis
  • Crystallography

Background:

  • Diazonium compounds are widely used as energetic materials.
  • However, many diazonium compounds suffer from poor thermal stability and high sensitivity.
  • There is a need for safer, more stable diazonium-based energetic materials.

Purpose of the Study:

  • To synthesize and characterize a novel insensitive diazonium inner salt.
  • To evaluate the thermal stability and mechanical sensitivity of the new compound.
  • To understand the structural factors contributing to its improved safety properties.

Main Methods:

  • A three-step synthetic route was employed for NTPD synthesis.
  • Single-crystal X-ray diffraction was used to determine the crystal structure.
  • Thermal stability was assessed by onset decomposition temperature, and mechanical sensitivity by impact testing.

Main Results:

  • A novel diazonium inner salt, NTPD, was successfully synthesized.
  • NTPD exhibits a fused-ring framework with an intramolecular zwitterionic structure.
  • It shows an onset decomposition temperature of 206 °C and an impact sensitivity of 7 J, indicating high thermal stability and low sensitivity.

Conclusions:

  • NTPD is a promising insensitive energetic material with superior thermal stability and reduced mechanical sensitivity compared to conventional diazonium compounds.
  • Its planar molecular geometry and extensive hydrogen-bonding network contribute to its enhanced safety.
  • This research offers a new avenue for developing safer energetic materials.