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

Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

3.3K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
3.3K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

3.6K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
3.6K
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

18.9K
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds,...
18.9K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.4K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.4K
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

3.6K
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
3.6K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.9K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.9K

You might also read

Related Articles

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

Sort by
Same author

Developmental exposure to a human-relevant PCB mixture: impacts on PCB congeners, metabolites, and drug-metabolizing enzymes in the bladder of post-weaning mice.

Archives of toxicology·2026
Same author

Morphological, Behavioral, and Transcriptomic Profiling Reveals Developmental Toxicity of PCB Metabolites in Zebrafish.

Toxics·2026
Same author

Neuroprotection Against a Panel of Toxicants via a Novel Analog of the Natural Product Fraxinellone.

Chemical research in toxicology·2026
Same author

BENOXACOR IS ENANTIOSELECTIVELY METABOLIZED BY MICROSOMES AND CYTOSOL FROM THE HUMAN LIVER.

Emerging contaminants·2026
Same author

Emergency Preparedness in Older Adults With and Without COPD During Power Outages and Natural Disasters.

Journal of applied gerontology : the official journal of the Southern Gerontological Society·2026
Same author

Spatial transcriptomic profiling uncovers the molecular effects of the neurotoxicant polychlorinated biphenyls (PCBs) in the brains of adult mice.

Molecular psychiatry·2026

Related Experiment Video

Updated: Oct 15, 2025

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

14.1K

3-(3,5-Dichlorophenyl)benzene-1,2-diol.

Ram Dhakal1, Sean Parkin2, Hans-Joachim Lehmler1

  • 1The University of Iowa, Department of Occupational and Environmental Health, University of Iowa Research Park, Iowa City, IA 52242, USA.

Iucrdata
|October 28, 2021
PubMed
Summary
This summary is machine-generated.

This study identifies 4-(3,5-dichlorophenyl)benzene-1,2-diol as a potential metabolite of 3,5-dichlorobiphenyl (PCB 14). Structural analysis reveals specific hydrogen bonding interactions in its crystalline form.

More Related Videos

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
07:06

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

11.6K
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

13.1K

Related Experiment Videos

Last Updated: Oct 15, 2025

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

14.1K
Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
07:06

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

11.6K
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

13.1K

Area of Science:

  • Environmental Chemistry
  • Crystallography
  • Metabolomics

Background:

  • Polychlorinated biphenyls (PCBs) are persistent organic pollutants with known environmental and health concerns.
  • Understanding PCB metabolism is crucial for assessing their toxicological impact and environmental fate.
  • 3,5-dichlorobiphenyl (PCB 14) is a specific congener whose metabolic pathways require further elucidation.

Purpose of the Study:

  • To characterize the chemical structure and properties of a putative metabolite of 3,5-dichlorobiphenyl (PCB 14).
  • To investigate the structural features, including dihedral angles and intermolecular interactions, of the identified compound.
  • To provide insights into the potential metabolic transformation pathways of PCBs.

Main Methods:

  • Chemical synthesis and characterization of 4-(3,5-dichlorophenyl)benzene-1,2-diol.
  • Single-crystal X-ray diffraction to determine the molecular structure and crystal packing.
  • Analysis of dihedral angles between aromatic rings.
  • Identification and analysis of hydrogen bonding networks (O-H···O and O-H···Cl).

Main Results:

  • The systematic name 4-(3,5-dichlorophenyl)benzene-1,2-diol and chemical formula C12H8Cl2O2 were assigned to the putative PCB 14 metabolite.
  • The dihedral angle between the two benzene rings was determined to be 58.86(4)°.
  • Intra- and intermolecular O-H···O hydrogen bonds were observed, along with intermolecular O-H···Cl hydrogen···chlorine interactions.

Conclusions:

  • 4-(3,5-dichlorophenyl)benzene-1,2-diol is proposed as a significant metabolite of 3,5-dichlorobiphenyl (PCB 14).
  • The crystal structure reveals specific conformational preferences and intermolecular interactions that influence its solid-state properties.
  • This structural information contributes to a better understanding of PCB biodegradation and metabolic activation.