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

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

4.2K
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...
4.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.5K
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.
3.5K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

8.0K
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...
8.0K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.9K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

3.1K
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,...
3.1K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.9K

You might also read

Related Articles

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

Sort by
Same author

Bespoke library docking for 5-HT<sub>2A</sub> receptor agonists with antidepressant activity.

Nature·2022
Same author

Isomeric triazines exhibit unique profiles of bioorthogonal reactivity.

Chemical science·2020
Same author

Rh(III)-Catalyzed Aryl and Alkenyl C-H Bond Addition to Diverse Nitroalkenes.

ACS catalysis·2017
Same author

Building better bioorthogonal reactions.

Current opinion in chemical biology·2014
Same author

Isomeric cyclopropenes exhibit unique bioorthogonal reactivities.

Journal of the American Chemical Society·2013
Same author

Functionalized cyclopropenes as bioorthogonal chemical reporters.

Journal of the American Chemical Society·2012

Related Experiment Video

Updated: Apr 9, 2026

Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry
10:54

Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry

Published on: February 4, 2017

8.7K

1,2,4-Triazines Are Versatile Bioorthogonal Reagents.

David N Kamber, Yong Liang, Robert J Blizzard1

  • 1#Department of Biochemistry and Biophysics, Oregon State University, Corvallis, Oregon 97331, United States.

Journal of the American Chemical Society
|June 19, 2015
PubMed
Summary
This summary is machine-generated.

Researchers developed novel 1,2,4-triazine reagents for bioorthogonal chemistry. These stable compounds react efficiently with trans-cyclooctene (TCO), enabling applications in protein production and tandem reactions.

More Related Videos

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging
10:47

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

Published on: February 3, 2015

9.5K
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

11.0K

Related Experiment Videos

Last Updated: Apr 9, 2026

Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry
10:54

Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry

Published on: February 4, 2017

8.7K
Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging
10:47

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

Published on: February 3, 2015

9.5K
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

11.0K

Area of Science:

  • Chemical Biology
  • Organic Chemistry

Background:

  • Bioorthogonal chemistry enables studying biological systems using synthetic tools.
  • Existing bioorthogonal reactions face limitations in stability and scope.

Purpose of the Study:

  • To introduce a new class of bioorthogonal reagents: 1,2,4-triazines.
  • To evaluate their stability and reactivity in biological contexts.

Main Methods:

  • Synthesis and characterization of 1,2,4-triazine derivatives.
  • Assessment of reactivity with trans-cyclooctene (TCO).
  • Application in recombinant protein production and tandem bioorthogonal reactions.

Main Results:

  • 1,2,4-triazines exhibit high stability in biological media.
  • Demonstrated robust cycloaddition reactions with TCO.
  • Successful integration into recombinant protein labeling and multi-reaction schemes.

Conclusions:

  • 1,2,4-triazines represent a valuable addition to the bioorthogonal chemistry toolkit.
  • Their stability and reactivity expand possibilities for in vivo and in vitro applications.
  • This work addresses current limitations in bioorthogonal reagent design.