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

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

7.1K
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.
7.1K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.7K
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.
4.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.5K
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...
3.5K
Nitrosation of Enols01:19

Nitrosation of Enols

4.8K
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.
4.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.2K
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.
4.2K
Preparation of Nitriles01:12

Preparation of Nitriles

2.2K
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...
2.2K

You might also read

Related Articles

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

Sort by
Same author

Direct Electrochemical Synthesis of Tetrahydroisoquinolines through Shono-Type Oxidation.

Organic letters·2026
Same author

Uncovering the Role of Biological Sex in the Divergent Genetic Profiles of Early and Late-Diagnosed Autism.

Research square·2026
Same author

Nickel Foam Electrodes-A Versatile, Powerful, and Readily Available Tool in Electro-Organic Synthesis.

Chemical record (New York, N.Y.)·2026
Same author

Simple and Scalable Electrochemical Reduction of Alkyl Oxalates Using Carbon-Based Electrodes.

ChemSusChem·2026
Same author

Silica Sol-Gel Coatings for Solar Panels: Drop Friction and Particle Adhesion.

ACS applied materials & interfaces·2026
Same author

Electrochemical Synthesis of 1,2-Substituted <i>N</i>-Amido Benzimidazoles by Reduction of Nitroarenes.

Organic letters·2026

Related Experiment Video

Updated: Oct 18, 2025

Measuring Nitrite and Nitrate, Metabolites in the Nitric Oxide Pathway, in Biological Materials using the Chemiluminescence Method
08:25

Measuring Nitrite and Nitrate, Metabolites in the Nitric Oxide Pathway, in Biological Materials using the Chemiluminescence Method

Published on: December 25, 2016

22.7K

Electrochemical Nitration with Nitrite.

Stephan P Blum1, Christean Nickel1, Lukas Schäffer1

  • 1Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.

Chemsuschem
|September 28, 2021
PubMed
Summary
This summary is machine-generated.

This study introduces an electrochemical method for aromatic nitration using tetrabutylammonium nitrite (NBu4NO2) as a safe nitro source. The process, enhanced by hexafluoroisopropanol (HFIP), offers high yields and scalability for producing valuable nitroaromatic compounds.

Keywords:
electrochemistrygreen chemistrynitrogen oxidesradicalssynthetic methods

More Related Videos

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
08:23

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

Published on: February 16, 2022

4.4K
Analytical Techniques for Assaying Nitric Oxide Bioactivity
11:28

Analytical Techniques for Assaying Nitric Oxide Bioactivity

Published on: June 18, 2012

18.2K

Related Experiment Videos

Last Updated: Oct 18, 2025

Measuring Nitrite and Nitrate, Metabolites in the Nitric Oxide Pathway, in Biological Materials using the Chemiluminescence Method
08:25

Measuring Nitrite and Nitrate, Metabolites in the Nitric Oxide Pathway, in Biological Materials using the Chemiluminescence Method

Published on: December 25, 2016

22.7K
Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
08:23

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

Published on: February 16, 2022

4.4K
Analytical Techniques for Assaying Nitric Oxide Bioactivity
11:28

Analytical Techniques for Assaying Nitric Oxide Bioactivity

Published on: June 18, 2012

18.2K

Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Chemistry

Background:

  • Nitroaromatic compounds are essential intermediates in organic synthesis.
  • Traditional nitration methods often involve hazardous reagents and conditions.
  • Developing safer and more efficient nitration techniques is crucial.

Purpose of the Study:

  • To develop a novel electrochemical method for aromatic nitration.
  • To utilize tetrabutylammonium nitrite (NBu4NO2) as a dual-purpose reagent (supporting electrolyte and nitro source).
  • To enhance reaction efficiency using solvent control with 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP).

Main Methods:

  • Electrochemical oxidation of NBu4NO2 in acetonitrile (MeCN) to generate the nitrating species (NO2).
  • Utilizing a divided electrolysis cell with inexpensive graphite electrodes.
  • Employing stoichiometric amounts of HFIP to improve reaction yields.

Main Results:

  • Successful electrochemical nitration of aromatic compounds demonstrated for 20 examples.
  • Achieved yields of up to 88% for the synthesized nitroaromatic compounds.
  • Demonstrated scalability of the electrochemical nitration process with a 13-fold scale-up.

Conclusions:

  • Electrochemical nitration using NBu4NO2 offers a safe, efficient, and scalable alternative to traditional methods.
  • The combination of NBu4NO2 and HFIP provides excellent control and high yields in aromatic nitration.
  • This method provides a versatile route to valuable nitroaromatic building blocks.