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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction at the stage of...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the electrophilic halogen to produce...
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...

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Related Experiment Video

Updated: May 16, 2026

Detection of Regulated Ergot Alkaloids in Food Matrices by Liquid Chromatography-Trapped Ion Mobility Spectrometry-Time-of-Flight Mass Spectrometry
08:56

Detection of Regulated Ergot Alkaloids in Food Matrices by Liquid Chromatography-Trapped Ion Mobility Spectrometry-Time-of-Flight Mass Spectrometry

Published on: November 22, 2024

Occurrence of halogenated alkaloids.

Gordon W Gribble1

  • 1Department of Chemistry, Dartmouth College, Hanover, New Hampshire, USA. ggribble@dartmouth.edu

The Alkaloids. Chemistry and Biology
|November 30, 2012
PubMed
Summary

Naturally occurring organohalogen compounds, especially halogenated alkaloids, are increasingly discovered and show potent biological activity. Research into marine and terrestrial sources continues to reveal new compounds with significant potential.

Area of Science:

  • Natural Product Chemistry
  • Marine Biology
  • Medicinal Chemistry

Background:

  • Naturally occurring organohalogen compounds were once dismissed but now exceed 5000, with over 25% being halogenated alkaloids.
  • Nitrogen-containing compounds like pyrroles and indoles serve as ideal substrates for biohalogenation, particularly in marine environments rich in chloride and bromide.

Purpose of the Study:

  • To review the occurrence of halogenated alkaloids, excluding marine bromotyrosines.
  • To highlight the expanding class of natural products and their biological significance.

Main Methods:

  • Literature review of existing studies on halogenated alkaloids.
  • Focus on occurrence, with brief mentions of biological activity and future synthesis coverage.

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Applications of Liquid-Chromatography Tandem Mass Spectrometry in Natural Products Research: Tropane Alkaloids as a Case Study
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Applications of Liquid-Chromatography Tandem Mass Spectrometry in Natural Products Research: Tropane Alkaloids as a Case Study

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Source and Route of Pyrrolizidine Alkaloid Contamination in Tea Samples
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Source and Route of Pyrrolizidine Alkaloid Contamination in Tea Samples

Published on: September 28, 2022

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Last Updated: May 16, 2026

Detection of Regulated Ergot Alkaloids in Food Matrices by Liquid Chromatography-Trapped Ion Mobility Spectrometry-Time-of-Flight Mass Spectrometry
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Detection of Regulated Ergot Alkaloids in Food Matrices by Liquid Chromatography-Trapped Ion Mobility Spectrometry-Time-of-Flight Mass Spectrometry

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Applications of Liquid-Chromatography Tandem Mass Spectrometry in Natural Products Research: Tropane Alkaloids as a Case Study
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Applications of Liquid-Chromatography Tandem Mass Spectrometry in Natural Products Research: Tropane Alkaloids as a Case Study

Published on: March 8, 2024

Source and Route of Pyrrolizidine Alkaloid Contamination in Tea Samples
06:04

Source and Route of Pyrrolizidine Alkaloid Contamination in Tea Samples

Published on: September 28, 2022

Main Results:

  • Over 5000 naturally occurring organohalogen compounds identified, with >25% being halogenated alkaloids.
  • Halogenated alkaloids are prevalent in marine and terrestrial environments, with significant biological activity.
  • Advancements in research methods, collection techniques, and a renewed interest in traditional medicine drive discovery.

Conclusions:

  • The discovery of halogenated alkaloids is rapidly expanding due to improved research tools and exploration of diverse natural sources.
  • Marine organisms and fungi represent vast, underexplored reservoirs of novel halogenated alkaloids.
  • The continued investigation of these compounds promises significant contributions to drug discovery and natural product chemistry.