Anthracene

Jump to navigation Jump to search

Template:Chembox new

WikiDoc Resources for Anthracene

Articles

Most recent articles on Anthracene

Most cited articles on Anthracene

Review articles on Anthracene

Articles on Anthracene in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Anthracene

Images of Anthracene

Photos of Anthracene

Podcasts & MP3s on Anthracene

Videos on Anthracene

Evidence Based Medicine

Cochrane Collaboration on Anthracene

Bandolier on Anthracene

TRIP on Anthracene

Clinical Trials

Ongoing Trials on Anthracene at Clinical Trials.gov

Trial results on Anthracene

Clinical Trials on Anthracene at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Anthracene

NICE Guidance on Anthracene

NHS PRODIGY Guidance

FDA on Anthracene

CDC on Anthracene

Books

Books on Anthracene

News

Anthracene in the news

Be alerted to news on Anthracene

News trends on Anthracene

Commentary

Blogs on Anthracene

Definitions

Definitions of Anthracene

Patient Resources / Community

Patient resources on Anthracene

Discussion groups on Anthracene

Patient Handouts on Anthracene

Directions to Hospitals Treating Anthracene

Risk calculators and risk factors for Anthracene

Healthcare Provider Resources

Symptoms of Anthracene

Causes & Risk Factors for Anthracene

Diagnostic studies for Anthracene

Treatment of Anthracene

Continuing Medical Education (CME)

CME Programs on Anthracene

International

Anthracene en Espanol

Anthracene en Francais

Business

Anthracene in the Marketplace

Patents on Anthracene

Experimental / Informatics

List of terms related to Anthracene

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Overview

Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings derived from coal-tar. Anthracene is used in the artificial production of the red dye alizarin. It is also used in wood preservatives, insecticides, and coating materials. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet light.

Synthesis

A classic method for the preparation of anthracene in the laboratory is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction (named for the German chemist Karl Elbs).

Reactions

Anthracene has the ability to photodimerize with irradiation by UV light. This results in considerable changes in the physical properties of the material.

Anthracene dimer
Anthracene dimer

The dimer is connected by two covalent bonds resulting from the [4+4] cycloaddition. The dimer reverts to anthracene thermally or with UV irradiation below 300 nm. The reversible bonding and photochromic properties of anthracenes is the basis of many potential applications using poly and monosubstituted anthracene derivatives. The reaction is sensitive to oxygen.

In most other reactions of anthracene, the central ring is also targeted, as it is the most highly reactive. Electrophilic substitution occurs at the "9" and "10" positions of the center ring, and oxidation of anthracene occurs readily, giving anthraquinone, C14H8O2 (below).

Anthraquione
Anthraquione

Uses

Anthracene can also have a hydroxyl group to form 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and napthol, and hydroxyanthracene is also called anthrol, and anthracenol.[1][2] Hydroxyanthracene derivatives are pharmacologically active, and are contained in aloe for example.[3][4]

Anthracene is an organic semiconductor.

Anthracene is used as a scintillator for detectors of high energy photons, electrons and alpha particles. Plastics such as polyvinyltolulene can be doped with Anthracene to produce a plastic scintillator that is approximately water equivalent for use in radiation therapy dosimetry. Anthracenes emission spectrum peaks at between 400 nm and 440 nm.

See also

References

External links


cs:Antracen de:Anthracen it:Antracene nl:Anthraceen fi:Antraseeni uk:Антрацен


Template:WS