Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.3K
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.
4.3K
Preparation of Nitriles01:12

Preparation of Nitriles

2.1K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.1K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.0K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.0K
Nitrosation of Enols01:19

Nitrosation of Enols

2.9K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
2.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.8K
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.
3.8K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.7K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
3.7K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

3D potassium energetic metal-organic framework enables safer lead-free primary energetic materials with positive oxygen balance.

Materials horizons·2026
Same author

Nitroimine-encoded conformational locking: a molecular switch for planarity and stability.

Materials horizons·2026
Same author

Synthesis, characterization, DFT calculations, and crystal structure of [Ru<sub>2</sub>(O<sub>2</sub>CCF<sub>3</sub>)<sub>2</sub>(CO)<sub>4</sub> <i>L</i> <sub>2</sub>]: tri-fluoro-acetate-bridged dimeric ruthenium(I) sawhorse complexes bearing phosphine ligands.

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

Topological Control of Dual Protonic-Electronic Conduction in Metal-Organic Frameworks.

Journal of the American Chemical Society·2026
Same author

Thermally driven tetrazine-to-triazole ring contraction mediated by hydroxylammonium cations.

Materials horizons·2026
Same author

Potassium trinitromethyl tetrazole (TNMT-K): a new member of the primary explosive family.

Materials horizons·2026

Related Experiment Video

Updated: Jul 11, 2025

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
09:05

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

14.8K

Manipulating nitration and stabilization to achieve high energy.

Jatinder Singh1, Richard J Staples2, Jean'ne M Shreeve1

  • 1Department of Chemistry, University of Idaho, Moscow, ID 83844-2343 USA.

Science Advances
|November 15, 2023
PubMed
Summary

Researchers synthesized the first azole molecule with seven nitro groups, paving the way for advanced energetic materials. This highly nitrated compound offers exceptional density and a positive oxygen balance, advancing the field of energetic materials.

More Related Videos

Preparation and Reactivity of Gasless Nanostructured Energetic Materials
09:50

Preparation and Reactivity of Gasless Nanostructured Energetic Materials

Published on: April 2, 2015

10.3K
A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

10.1K

Related Experiment Videos

Last Updated: Jul 11, 2025

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
09:05

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

14.8K
Preparation and Reactivity of Gasless Nanostructured Energetic Materials
09:50

Preparation and Reactivity of Gasless Nanostructured Energetic Materials

Published on: April 2, 2015

10.3K
A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

10.1K

Area of Science:

  • Energetic Materials Science
  • Organic Chemistry
  • Nitration Chemistry

Background:

  • Nitro groups are crucial for developing powerful energetic materials.
  • Highly nitrated compounds can serve as environmentally safer alternatives to hazardous oxidizers like ammonium perchlorate.
  • Azole compounds with extensive nitration are scarce due to thermal instability and limited functionalization sites.

Purpose of the Study:

  • To synthesize and characterize a novel azole molecule with a high degree of nitration.
  • To explore the potential of highly nitrated azoles as advanced energetic materials.

Main Methods:

  • Stepwise nitration of 3,5-dimethyl-1H-pyrazole.
  • Characterization of the resulting highly nitrated azole compound.

Main Results:

  • Formation of the first azole molecule with seven nitro groups: 4-nitro-3,5-bis(trinitromethyl)-1H-pyrazole.
  • Compound exhibits exceptional physicochemical properties, including a positive oxygen balance (OBCO2 = 13.62%).
  • Achieved an extremely high calculated density of 2.04 g cm-3 at 100 K for a C, H, N, O compound.

Conclusions:

  • This work represents a significant advancement in the synthesis of highly nitrated and dense azoles.
  • The novel compound's properties suggest potential applications in energetic materials.
  • Accelerates further research in the challenging field of high-nitrogen energetic compounds.