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Anthracene

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Anthracene
Skeletal formula and numbering system of anthracene
Skeletal formula and numbering system of anthracene
Ball-and-stick model of the anthracene molecule
Anthracene
Anthracene
Names
IUPAC name
Anthracene
Identifiers
3D model (JSmol)
1905429
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.974 Edit this at Wikidata
EC Number
  • 217-004-5
67837
KEGG
RTECS number
  • CA9350000
UNII
UN number 3077
  • InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H checkY
    Key: MWPLVEDNUUSJAV-UHFFFAOYSA-N checkY
  • InChI=1/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H
    Key: MWPLVEDNUUSJAV-UHFFFAOYAK
  • c1ccc2cc3ccccc3cc2c1
Properties[1]
C14H10
Molar mass 178.234 g·mol−1
Appearance Colorless
Odor Weak aromatic
Density 1.28 g/cm3
Melting point 216 ± 2 °C (421 ± 4 °F; 489 ± 2 K)
Boiling point 341.3 ± 0.4 °C (646.3 ± 0.7 °F; 614.5 ± 0.4 K)
Insoluble (2.2 μg/100 g)
Solubility in pressurized hot water
  • 0.0101 % mass (150 °C (302 °F), 50 bar)
  • 0.49 % mass (250 °C (482 °F), 50 bar)
  • 3.62 % mass (300 °C (572 °F), 100 bar)
Solubility in benzene 1.86 g/100 g[2]
Solubility in carbon disulphide 2.58 g/100 g[2]
Solubility in diethyl ether 1.42 g/100 g[2]
Solubility in ethanol 0.328 g/100 g[2]
Solubility in toluene
  • 0.92 g/100 g (16.5 °C (61.7 °F))
  • 12.94 g/100 g (100 °C (212 °F))[2]
log P 4.56
Vapor pressure
  • 1 Pa (89.2 °C (192.6 °F), subl.)
  • 100 Pa (151.5 °C (304.7 °F), subl.)
  • 1 kPa (165 °C (329 °F), subl.)
  • 10 kPa (238.8 °C (461.8 °F))
  • 100 kPa (340.2 °C (644.4 °F))
0.00396 (kPa·m3)/mol
Electrical resistivity 1.5×1011 Ω·cm
UV-vis (λmax) 252 nm, 375 nm
Band gap 2.50 eV
Electron mobility 2.3 cm2/(V·s)
129.8×10−6 cm3/mol
Structure (290 K)[3]
Monoclinic
P21/b
C2h
a = 8.562 Å, b = 6.038 Å, c = 11.184 Å
α = 90°, β = 124.7°, γ = 90°
2
Structure (metastable from vapor growth)[4]
Monoclinic
P21/n
a = 8.553 Å, b = 6.021 Å, c = 22.334 Å
α = 90°, β = 124.54°, γ = 90°
4
Thermochemistry[1]
210.5 J⋅mol−1⋅K−1
207.5 J⋅mol−1⋅K−1
  • 129.2 kJ⋅mol−1 (solid)
  • 230.9 kJ⋅mol−1 (gas)
7068 kJ⋅mol−1
Enthalpy of fusion (ΔfH⦵fus)
 29.4 kJ⋅mol−1
Hazards
GHS labelling:[5]
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
NFPA 704 (fire diamond)
[6]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Flash point 121 °C (250 °F; 394 K)[1]
540 °C (1,004 °F; 813 K)[1]
Explosive limits >0.6%[1]
Lethal dose or concentration (LD, LC):
  • 4900 mg/kg (rat, oral)[5]
  • >1320 mg/kg (rat, dermal)[6]
NIOSH (US health exposure limits):[5]
PEL (Permissible)
 0.2 mg/m3 (TWA)
REL (Recommended)
 0.1 mg/m3 (TWA)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

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 as a precursor in the production of anthraquinone and its derivatives such as the red dye alizarin, and as a scintillator to detect high energy particles. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.[7]

History and etymology

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Crude anthracene (with a melting point of only 180°) was discovered in 1832 by Jean-Baptiste Dumas and Auguste Laurent[8] 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,[9] which is translated to English as paranaphthalene.[8] 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.[10] This notion was disproved in 1850s and 1860s.[11][12]

Occurrence and production

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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.[13] 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.[14]

Reactions

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Reduction

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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.[15]

Cycloadditions

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In any solvent except water,[16] anthracene photodimerizes by the action of UV light:

Anthracene dimer

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.[17][18]

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

Diels alder reaction of anthracene with singlet oxygen
Diels alder reaction of anthracene with singlet oxygen

With electrophiles

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Chemical oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate.[19]

Anthraquione
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.[20] Bromination of anthracene gives 9,10-dibromoanthracene.[21]

Uses

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

Electronics

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Fluorescence of anthracene under UV light

Anthracene is a wide band-gap organic semiconductor, with an emission spectrum peaking in the dark violet (400 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.[22] 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.[23]

Derivatives

[edit]
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.[24] Derivatives having a hydroxyl group are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and naphthols, and hydroxyanthracene (also called anthrol, and anthracenol)[25][26] are pharmacologically active.

Anthracene may also be found with multiple hydroxyl groups, as in 9,10-dihydroxyanthracene.

Some anthracene derivatives are used as pharmaceuticals, including the chemotherapeutic agent bisantrene, and benzoctamine.


Toxicology

[edit]

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.[24] Nevertheless, the International Agency for Research on Cancer (IARC) classifies anthracene as IARC group 2B, possibly carcinogenic to humans.[27]

Anthracene is readily biodegraded in soil. It is especially susceptible to degradation in the presence of light.[24]

See also

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References

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  1. 1 2 3 4 5 Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton, Florida: CRC Press. pp. 3–28, 3–576, 5–5, 5–67, 5–140, 5–173, 5–182, 6–95, 6–98, 8–38, 12–95, 16–17. ISBN 9781498754293.
  2. 1 2 3 4 5 Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). New York: D. Van Nostrand Company. p. 81.
  3. ↑ Douglas, Bodie E.; Ho, Shih-Ming (2007). Structure and Chemistry of Crystalline Solids. New York: Springer Science+Business Media, Inc. p. 289. ISBN 978-0-387-26147-8.
  4. ↑ Marciniak, B.; Pavlyuk, V. (1 January 2002). "Crystal Structure of a Metastable Anthracene Modification, Grown from the Vapor Phase". Molecular Crystals and Liquid Crystals. 373 (1): 237–250. doi:10.1080/10587250210538.
  5. 1 2 3 Sigma-Aldrich Co., Anthracene.
  6. 1 2 "SDS - Anthracene". www.fishersci.com. Revision 9. ThermoFisher Scientific. 18 December 2025 [3 May 2012]. Retrieved 19 July 2026.
  7. ↑ Lindsey, Jonathan; et al. "Anthracene". PhotochemCAD. Retrieved 20 February 2014.
  8. 1 2 Wisniak, Jaime (2009). "Auguste Laurent: Radical and radicals". Educación química. 20 (2): 166–175. doi:10.1016/S0187-893X(18)30023-5. ISSN 0187-893X.
  9. ↑ fr:Comptes rendus de l'Académie des sciences/Tome 1, 1835/7 décembre  – via Wikisource.
  10. ↑ Annales de chimie et de physique (in French). 1837.
  11. ↑ "À propos de l'anthracène et de l'alizarine – p3 – N°467 – L'Actualité Chimique, le journal de la SCF". Société Chimique de France (SCF) (in French). Retrieved 2024-11-11.
  12. ↑ 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. ISSN 0199-9818. JSTOR 25138602.
  13. ↑ Freitalite, Mindat, https://www.mindat.org/min-54360.html
  14. ↑ "Anthracene". American Chemical Society. Retrieved 2022-09-14.
  15. ↑ Bass, K. C. (1962). "9,10-Dihydroanthracene". Organic Syntheses. 42: 48. doi:10.15227/orgsyn.042.0048.
  16. ↑ Johnson, Keith E.; Pagni, Richard M., "Liquid salts for reactions", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, p. 28, doi:10.1002/0471238961.liqupagn.a01, ISBN 9780471238966
  17. ↑ 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.
  18. ↑ 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.
  19. ↑ 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. Bibcode:2011JChEd..88.1155C. doi:10.1021/ed100843a.
  20. ↑ 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.
  21. ↑ Heilbron, I. M.; Heaton, J. S. (1923). "9,10-Dibromoanthracene". Organic Syntheses. 3: 41. doi:10.15227/orgsyn.003.0041.
  22. ↑ "Anthracene". American Chemical Society. Retrieved 2025-01-18.
  23. ↑ Zeitler, Alex (27 June 2012). Conformal Coating 101: General Overview, Process Development, and Control Methods (PDF) (Technical report). BTW, Inc.
  24. 1 2 3 Collin, Gerd; Höke, Hartmut; Talbiersky, Jörg (2006). "Anthracene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_343.pub2. ISBN 978-3-527-30673-2.
  25. ↑ "1-Hydroxyanthracene - NIST datapage". webbook.nist.gov. US National Institute of Standards.
  26. ↑ "2-Hydroxyanthracene - NIST datapage". webbook.nist.gov. US National Institute of Standards.
  27. ↑ "IARC Monographs evaluate the carcinogenicity of anthracene, 2-bromopropane, butyl methacrylate, and dimethyl hydrogen phosphite". www.iarc.who.int. Retrieved 2025-01-17.
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