Anthracene

Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes, as a scintillator to detect high energy particles, as production of pharmaceutical drugs. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.[1]

## Contents

* 1 History and etymology
* 2 Occurrence and production
* 3 Reactions
* 3.1 Reduction
* 3.2 Cycloadditions
* 3.3 With electrophiles
* 4 Uses
* 4.1 Electronics
* 4.2 Derivatives
* 5 Toxicology
* 6 See also
* 7 References
* 8 Cited sources
* 9 External links

## History and etymology

Crude anthracene (with a melting point of only 180°) was discovered in 1832 by Jean-Baptiste Dumas and Auguste Laurent[2] who crystalized it from a fraction of coal tar later known as "anthracene oil". Since their (inaccurate) measurements showed the proportions of carbon and hydrogen of it to be the same as in naphthalene, Laurent called it paranaphtaline in his 1835 publication of the discovery,[3] which is translated to English as paranaphthalene.[2] Two years later, however, he decided to rename the compound to its modern name derived from Ancient Greek: ἄνθραξ, romanized: anthrax, lit. 'coal' because after discovering other polyaromatic hydrocarbons he decided it was only one of isomers of naphthalene.[4] This notion was disproved in 1850s and 1860s.[5][6]

## Occurrence and production

Anthracene, as many other polycyclic aromatic hydrocarbons, is generated during combustion processes. Most human exposure is through tobacco smoke or ingestion of charred food.

The mineral form of anthracene is called freitalite and is related to a coal deposit.[7] Coal tar, which contains around 1.5% anthracene, remains a major industrial source of this material. Common impurities are phenanthrene and carbazole.

A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from o-tolyl phenyl ketone.[8]

## Reactions

### Reduction

Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]− (M = Li, Na, K). Reduction with sodium in ethanol gives 9,10-dihydroanthracene, preserving the aromaticity of the two flanking rings.[9]

### Cycloadditions

In any solvent except water,[10] anthracene photodimerizes by the action of UV light:

The dimer, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the [4+4] cycloaddition. It reverts to anthracene thermally or with UV irradiation below 300 nm. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of oxygen.[11][12]

Anthracene also reacts with dienophile singlet oxygen in a [4+2]-cycloaddition (Diels–Alder reaction):

Diels alder reaction of anthracene with singlet oxygen

### With electrophiles

Chemical oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate.[13]

Anthraquione

Electrophilic substitution of anthracene occurs at the 9 position. For example, formylation affords 9-anthracenecarboxaldehyde. Substitution at other positions is effected indirectly, for example starting with anthroquinone.[14] Bromination of anthracene gives 9,10-dibromoanthracene.[15]

## Uses

Anthracene proper has application as an organic semiconductor and chemical feedstock for various preservatives and dyes.

### Electronics

Fluorescence of anthracene under UV light

Anthracene is a wide band-gap organic semiconductor, with an emission spectrum peaking between 400 nm and 440 nm. Organic field-effect transistors have been constructed from it. In particle physics, it is used as a scintillator to detect high-energy photons, electrons, or alpha particles.[16] Plastics, such as polyvinyltoluene, can be doped with anthracene to produce an approximately water-equivalent scintillator in radiation therapy dosimetry.

Anthracene is commonly used as a UV tracer in conformal coatings applied to printed wiring boards. The anthracene tracer allows the conformal coating to be inspected under UV light.[17]

### Derivatives

False-color AFM image of anthracene diradical, where hydrogen atoms are removed at carbons 9 and 10

A variety of anthracene derivatives find specialized uses. Industrially, anthracene is converted mainly to anthraquinone, a precursor to dyes.[18] Derivatives having a hydroxyl group are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and naphthols, and hydroxyanthracene (also called anthrol, and anthracenol)[19][20] are pharmacologically active. Anthracene may also be found with multiple hydroxyl groups, as in 9,10-dihydroxyanthracene.

Some anthracene derivatives are used as pharmaceutical drugs, including bisantrene, trazitiline, and benzoctamine.

## Toxicology

Many investigations indicate that anthracene is noncarcinogenic: "consistently negative findings in numerous in vitro and in vivo genotoxicity tests". Early experiments suggested otherwise because crude samples were contaminated with other polycyclic aromatic hydrocarbons.[18] Nevertheless, the International Agency for Research on Cancer (IARC) classifies anthracene as IARC group 2B, possibly carcinogenic to humans.[21]

Anthracene is readily biodegraded in soil. It is especially susceptible to degradation in the presence of light.[18]

## See also

* 9,10-Dithioanthracene, derivative with two thiol groups added to the central ring
* Phenanthrene
* Acridine
* Phenazine
* Tetracene

## References

1. ↑ Lindsey, Jonathan. "Anthracene". PhotochemCAD. http://omlc.ogi.edu/spectra/PhotochemCAD/html/022.html.
2. ↑ 2.0 2.1 Wisniak, Jaime (2009). "Auguste Laurent: Radical and radicals" (in en). Educación química 20 (2): 166–175. doi:10.1016/S0187-893X(18)30023-5. ISSN 0187-893X.
3. ↑ fr:Comptes rendus de l'Académie des sciences/Tome 1, 1835/7 décembre
4. ↑ (in fr) Annales de chimie et de physique. 1837. https://books.google.com/books?id=wZg5AAAAcAAJ&pg=PA149.
5. ↑ "À propos de l'anthracène et de l'alizarine – p3 – N°467 – L'Actualité Chimique, le journal de la SCF" (in fr-FR). https://new.societechimiquedefrance.fr/numero/a-propos-de-lanthracene-et-de-lalizarine-p3-n467.
6. ↑ Jackson, C. Loring; White, J. Fleming (1880). "Researches on the Substituted Benzyl Compounds. Ninth Paper. The Synthesis of Anthracene and Phenanthrene from Orthobrombenzylbromide". Proceedings of the American Academy of Arts and Sciences 16: 63–77. doi:10.2307/25138602. ISSN 0199-9818. https://www.jstor.org/stable/25138602.
7. ↑ Freitalite, Mindat, https://www.mindat.org/min-54360.html
8. ↑ "Anthracene" (in en). https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/anthracene.html.
9. ↑ Bass, K. C. (1962). "9,10-Dihydroanthracene". Organic Syntheses 42: 48. doi:10.15227/orgsyn.042.0048.
10. ↑ Johnson., Keith E.; Pagni, Richard M., "Liquid salts for reactions", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, doi:10.1002/0471238961.liqupagn.a01, ISBN 9780471238966, http://onlinelibrary.wiley.com/book/10.1002/0471238961
11. ↑ Rickborn, Bruce (1998). "The Retro–Diels–Alder Reaction Part I. C-C Dienophiles". Organic Reactions. pp. 1–393. doi:10.1002/0471264180.or052.01. ISBN 978-0-471-26418-7.
12. ↑ Bouas-Laurent, Henri; Desvergne, Jean-Pierre; Castellan, Alain; Lapouyade, Rene (2000). "Photodimerization of anthracenes in fluid solution: Structural aspects". Chemical Society Reviews 29: 43–55. doi:10.1039/a801821i.
13. ↑ Charleton, Kimberly D. M.; Prokopchuk, Ernest M. (2011). "Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)2". Journal of Chemical Education 88 (8): 1155–1157. doi:10.1021/ed100843a. Bibcode: 2011JChEd..88.1155C.
14. ↑ Škalamera, Đani; Veljković, Jelena; Ptiček, Lucija; Sambol, Matija; Mlinarić-Majerski, Kata; Basarić, Nikola (2017). "Synthesis of asymmetrically disubstituted anthracenes". Tetrahedron 73 (40): 5892–5899. doi:10.1016/j.tet.2017.08.038.
15. ↑ Heilbron, I. M.; Heaton, J. S. (1923). "9,10-Dibromoanthracene". Organic Syntheses 3: 41. doi:10.15227/orgsyn.003.0041.
16. ↑ "Anthracene" (in en). https://www.acs.org/molecule-of-the-week/archive/a/anthracene.html.
17. ↑ Zeitler, Alex (2012-06-27) Conformal Coating 101: General Overview, Process Development, and Control Methods. BTW, Inc.
18. ↑ 18.0 18.1 18.2 Collin, Gerd; Höke, Hartmut and Talbiersky, Jörg (2006) "Anthracene" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_343.pub2
19. ↑ 1-Hydroxyanthracene. NIST datapage
20. ↑ 2-Hydroxyanthracene. NIST datapage
21. ↑ "IARC Monographs evaluate the carcinogenicity of anthracene, 2-bromopropane, butyl methacrylate, and dimethyl hydrogen phosphite" (in en-US). https://www.iarc.who.int/faq/iarc-monographs-evaluate-the-carcinogenicity-of-anthracene-2-bromopropane-butyl-methacrylate-and-dimethyl-hydrogen-phosphite/#:~:text=Anthracene was classified as possibly,for cancer in experimental animals..

## Cited sources

* Haynes, William M., ed (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. ISBN 978-1-4398-5511-9.

## External links

| Wikisource has the text of the 1879 American Cyclopædia article Anthracene.

|

* International Chemical Safety Card 0825
* IARC – Monograph 32
* National Pollutant Inventory – Polycyclic Aromatic Hydrocarbon Fact Sheet
* European Chemicals Agency – ECHA

* v
* t
* e

Hydrocarbons

Saturated
aliphatic
hydrocarbons|

| Alkanes
CnH2n \+ 2|

| Linear alkanes|

* Methane
* Ethane
* Propane
* Butane
* Pentane
* Hexane
* Heptane
* Octane
* Nonane
* Decane

|

Branched alkanes|

* Isobutane
* Isopentane
* 3-Methylpentane
* Neopentane
* Isohexane
* Isoheptane
* Isooctane
* Isononane
* Isodecane

Cycloalkanes|

* Cyclopropane
* Cyclobutane
* Cyclopentane
* Cyclohexane
* Cycloheptane
* Cyclooctane
* Cyclononane
* Cyclodecane

Alkylcycloalkanes|

* Methylcyclopropane
* Methylcyclobutane
* Methylcyclopentane
* Methylcyclohexane
* Isopropylcyclohexane

Bicycloalkanes|

* Housane (bicyclo[2.1.0]pentane)
* Norbornane (bicyclo[2.2.1]heptane)
* Decalin (bicyclo[4.4.0]decane)

Polycycloalkanes|

* Adamantane
* Diamondoid
* Perhydrophenanthrene
* Sterane
* Cubane
* Prismane
* Dodecahedrane
* Basketane
* Churchane
* Pagodane
* Twistane

Other|

* Spiroalkanes

Unsaturated
aliphatic
hydrocarbons|

| Alkenes
CnH2n|

| Linear alkenes|

* Ethene
* Propene
* Butene
* Pentene
* Hexene
* Heptene
* Octene
* Nonene
* Decene

|

Branched alkenes|

* Isobutene
* Isopentene
* Isohexene
* Isoheptene
* Isooctene
* Isononene
* Isodecene

Alkynes
CnH2n − 2|

| Linear alkynes|

* Ethyne
* Propyne
* Butyne
* Pentyne
* Hexyne
* Heptyne
* Octyne
* Nonyne
* Decyne

|

Branched alkynes|

* Isopentyne
* Isohexyne
* Isoheptyne
* Isooctyne
* Isononyne
* Isodecyne

Cycloalkenes|

* Cyclopropene
* Cyclobutene
* Cyclopentene
* Cyclohexene
* Cycloheptene
* Cyclooctene
* Cyclononene
* Cyclodecene

Alkylcycloalkenes|

* Methylcyclopropene
* Methylcyclobutene
* Methylcyclopentene
* Methylcyclohexene
* Isopropylcyclohexene

Bicycloalkenes|

* Norbornene

Cycloalkynes|

* Cyclopropyne
* Cyclobutyne
* Cyclopentyne
* Cyclohexyne
* Cycloheptyne
* Cycloctyne
* Cyclononyne
* Cyclodecyne

Dienes|

* Propadiene
* Butadiene
* Pentadiene
* Hexadiene
* Heptadiene
* Octadiene
* Nonadiene
* Decadiene

Other|

* Alkatriene
* Alkadiyne
* Cumulene
* Cyclooctatetraene
* Cyclododecatriene
* Enyne

Aromatic
hydrocarbons|

| PAHs|

| Acenes|

* Naphthalene
* Anthracene
* Tetracene
* Pentacene
* Hexacene
* Heptacene

|

Other|

* Azulene
* Fluorene
* Helicenes
* Circulenes
* Butalene
* Phenanthrene
* Chrysene
* Pyrene
* Corannulene
* Kekulene

Alkylbenzenes|

* Toluene
* Xylene
* Ethylbenzene
* Cumene
* Styrene
* Mesitylene
* Pseudocumene
* Hemellitene
* Cymene
* Hexamethylbenzene

Other|

* Benzene
* Cyclopropenylidene

Other|

* Annulenes
* Annulynes
* Alicyclic compounds
* Petroleum jelly

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Tricyclics

Classes|

* Acridine
* Anthracene
* Dibenzazepine
* Dibenzocycloheptene
* Dibenzodiazepine
* Dibenzothiazepine
* Dibenzothiepin
* Dibenzoxazepine
* Dibenzoxepin
* Phenothiazine
* Pyridazinobenzoxazine
* Pyridinobenzodiazepine
* Thioxanthene

Antidepressants
(TCAs and TeCAs)|

* 7-OH-Amoxapine
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* Azipramine
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* Phenindamine
* Pimethixene
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Antipsychotics|

* Acetophenazine
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* Pentiapine
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* Perathiepin
* Perazine
* Perphenazine
* Periciazine
* Pinoxepin
* Piperacetazine
* Pipotiazine
* Piquindone
* Prochlorperazine
* Promazine
* Prothipendyl
* Quetiapine
* Savoxepin/Cipazoxapine
* Sulforidazine
* Tenilapine
* Thiethylperazine
* Thiopropazate
* Thioridazine
* Thiothixene
* Tilozepine
* Traboxopine
* Trifluoperazine
* Triflupromazine
* Trifluthepin
* Zotepine
* Zuclopenthixol

Anticonvulsants|

* Carbamazepine
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* Eslicarbazepine acetate
* Etazepine
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* Oxcarbazepine
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* Rispenzepine

Others|

* Adosopine
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* Methylene blue
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* P7C3
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* Profenamine
* Serazapine
* Siltenzepine
* Telenzepine
* Tipindole
* Tropatepine
* Zolenzepine

* v
* t
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Polycyclic aromatic hydrocarbons

2 rings|

* Butalene
* Azulene
* Naphthalene

3 rings|

* Acenaphthene
* Acenaphthylene
* Anthracene
* Fluorene
* Phenalene
* Phenanthrene

4 rings|

* Benz[a]anthracene
* Benzo[a]fluorene
* Benzo[c]fluorene
* Benzo[c]phenanthrene
* Chrysene
* Fluoranthene
* Pyrene
* Tetracene
* Triphenylene
* Tricyclobutabenzene

5 rings|

* Benz[e]acephenanthrylene
* Benzopyrene
* Benzo[a]pyrene
* Benzo[e]pyrene
* Benzo[a]fluoranthene
* Benzo[b]fluoranthene
* Benzo[j]fluoranthene
* Benzo[k]fluoranthene
* trans-Bicalicene
* Dibenz[a,h]anthracene
* Dibenz[a,j]anthracene
* Olympicene
* Pentacene
* Perylene
* Picene
* Tetraphenylene

6+ rings|

* Anthanthrene
* Benzo[ghi]perylene
* Circulene
* Corannulene
* Coronene
* Dicoronylene
* Diindenoperylene
* Heptacene
* Hexacene
* Kekulene
* Ovalene
* Zethrene

General classes|

* Acene
* Helicene
* Phenacene

* v
* t
* e

Molecules detected in outer space

Molecules|

| Diatomic|

* Aluminium monochloride
* Aluminium monofluoride
* Aluminium monoxide
* Argonium
* Carbon monophosphide
* Carbon monosulfide
* Carbon monoxide
* Carborundum
* Cyanogen radical
* Diatomic carbon
* Fluoromethylidynium
* Helium hydride ion
* Hydrogen chloride
* Hydrogen fluoride
* Hydrogen (molecular)
* Hydroxyl radical
* Iron(II) oxide
* Magnesium monohydride cation
* Methylidyne radical
* Nitric oxide
* Nitrogen (molecular)
* Nitrogen monohydride
* Nitrogen sulfide
* Oxygen (molecular)
* Phosphorus monoxide
* Phosphorus mononitride
* Potassium chloride
* Silicon carbide
* Silicon mononitride
* Silicon monoxide
* Silicon monosulfide
* Sodium chloride
* Sodium iodide
* Sulfur monohydride
* Sulfur monoxide
* Titanium oxide

|
|

Triatomic|

* Aluminium hydroxide
* Aluminium isocyanide
* Amino radical
* Carbon dioxide
* Carbonyl sulfide
* CCP radical
* Chloronium
* Diazenylium
* Dicarbon monoxide
* Disilicon carbide
* Ethynyl radical
* Formyl radical
* Hydrogen cyanide (HCN)
* Hydrogen isocyanide (HNC)
* Hydrogen sulfide
* Hydroperoxyl
* Iron cyanide
* Isoformyl
* Magnesium cyanide
* Magnesium isocyanide
* Methylene radical
* N2H+
* Nitrous oxide
* Nitroxyl
* Ozone
* Phosphaethyne
* Potassium cyanide
* Protonated molecular hydrogen
* Sodium cyanide
* Sodium hydroxide
* Silicon carbonitride
* c-Silicon dicarbide
* SiNC
* Sulfur dioxide
* Thioformyl
* Thioxoethenylidene
* Titanium dioxide
* Tricarbon
* Water

Four
atoms|

* Acetylene
* Ammonia
* Cyanic acid
* Cyanoethynyl
* Cyclopropynylidyne
* Formaldehyde
* Fulminic acid
* HCCN
* Hydrogen peroxide
* Hydromagnesium isocyanide
* Isocyanic acid
* Isothiocyanic acid
* Ketenyl
* Methylene amidogen
* Methyl radical
* Propynylidyne
* Protonated carbon dioxide
* Protonated hydrogen cyanide
* Silicon tricarbide
* Thioformaldehyde
* Tricarbon monoxide
* Tricarbon sulfide
* Thiocyanic acid

Five
atoms|

* Ammonium ion
* Butadiynyl
* Carbodiimide
* Cyanamide
* Cyanoacetylene
* Cyanoformaldehyde
* Cyanomethyl
* Cyclopropenylidene
* Formic acid
* Isocyanoacetylene
* Ketene
* Methane
* Methoxy radical
* Methylenimine
* Propadienylidene
* Protonated formaldehyde
* Protonated formaldehyde
* Silane
* Silicon-carbide cluster

Six
atoms|

* Acetonitrile
* Cyanobutadiynyl radical
* E-Cyanomethanimine
* Cyclopropenone
* Diacetylene
* Ethylene
* Formamide
* HC4N
* Ketenimine
* Methanethiol
* Methanol
* Methyl isocyanide
* Pentynylidyne
* Propynal
* Protonated cyanoacetylene

Seven
atoms|

* Acetaldehyde
* Acrylonitrile
* Vinyl cyanide
* Cyanodiacetylene
* Ethylene oxide
* Glycolonitrile
* Hexatriynyl radical
* Methylacetylene
* Methylamine
* Methyl isocyanate
* Vinyl alcohol

Eight
atoms|

* Acetic acid
* Aminoacetonitrile
* Cyanoallene
* Ethanimine
* Glycolaldehyde
* Heptatrienyl radical
* Hexapentaenylidene
* Methylcyanoacetylene
* Methyl formate
* Propenal

Nine
atoms|

* Acetamide
* Cyanohexatriyne
* Cyanotriacetylene
* Dimethyl ether
* Ethanol
* Methyldiacetylene
* Octatetraynyl radical
* Propene
* Propionitrile

Ten
atoms
or more|

* Acetone
* Benzene
* Benzonitrile
* Buckminsterfullerene (C60, C60+, fullerene, buckyball)
* C70 fullerene
* Cyanodecapentayne
* Cyanopentaacetylene
* Cyanotetra-acetylene
* Ethylene glycol
* Ethyl formate
* Methyl acetate
* Methyl-cyano-diacetylene
* Methyltriacetylene
* Propanal
* n-Propyl cyanide
* Pyrimidine

Deuterated
molecules|

* Ammonia
* Ammonium ion
* Formaldehyde
* Formyl radical
* Heavy water
* Hydrogen cyanide
* Hydrogen deuteride
* Hydrogen isocyanide
* Methylacetylene
* N2D+
* Trihydrogen cation

Unconfirmed|

* Anthracene
* Dihydroxyacetone
* Ethyl methyl ether
* Glycine
* Graphene
* H2NCO+
* Linear C5
* Naphthalene cation
* Phosphine
* Pyrene
* Silylidine

Related|

* Abiogenesis
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* Atomic and molecular astrophysics
* Chemical formula
* Circumstellar envelope
* Cosmic dust
* Cosmic ray
* Cosmochemistry
* Diffuse interstellar band
* Earliest known life forms
* Extraterrestrial life
* Extraterrestrial liquid water
* Forbidden mechanism
* Homochirality
* Intergalactic dust
* Interplanetary medium
* Interstellar medium
* Photodissociation region
* Iron–sulfur world theory
* Kerogen
* Molecules in stars
* Nexus for Exoplanet System Science
* Organic compound
* Outer space
* PAH world hypothesis
* Panspermia
* Polycyclic aromatic hydrocarbon (PAH)
* RNA world hypothesis
* Spectroscopy
* Tholin

* Category:Astrochemistry
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Original source: https://en.wikipedia.org/wiki/Anthracene. Read more

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