|Jmol-3D images||Image 1
|Molar mass||178.23 g mol−1|
|Density||1.28 g/cm3 (25 °C)
0.969 g/cm3 (220 °C)
|Melting point||215.76 °C (420.37 °F; 488.91 K)
at 760 mmHg
|Boiling point||339.9 °C (643.8 °F; 613.0 K)
at 760 mmHg
|Solubility in water||0.022 mg/L (0 °C)
0.044 mg/L (25 °C)
0.287 mg/L (50 °C)
0.00045% w/w (100 °C, 3.9 MPa)
|Solubility||Soluble in alcohol, (C2H5)2O, acetone, C6H6, CHCl3, CS2|
|Solubility in ethanol||0.076 g/100 g (16 °C)
1.9 g/100 g (19.5 °C)
0.328 g/100 g (25 °C)
|Solubility in methanol||1.8 g/100 g (19.5 °C)|
|Solubility in hexane||0.37 g/100 g|
|Solubility in toluene||0.92 g/100 g (16.5 °C)
12.94 g/100 g (100 °C)
|Solubility in carbon tetrachloride||0.732 g/100 g|
|Vapor pressure||0.01 kPa (125.9 °C)
0.1 kPa (151.5 °C)
13.4 kPa (250 °C)
|UV-vis (λmax)||345.6 nm, 363.2 nm|
|Thermal conductivity||0.1416 W/m·K (240 °C)
0.1334 W/m·K (270 °C)
0.1259 W/m·K (300 °C)
|Viscosity||0.602 cP (240 °C)
0.498 cP (270 °C)
0.429 cP (300 °C)
|Crystal structure||Monoclinic (290 K)|
|Lattice constant||a = 8.562 Å, b = 6.038 Å, c = 11.184 Å|
|Lattice constant||α = 90°, β = 124.7°, γ = 90°|
Std enthalpy of
Std enthalpy of
|GHS signal word||Warning|
|H315, H319, H335, H410|
|P261, P273, P305+351+338, P501|
|EU classification||Xi N|
|S-phrases||S26, S60, S61|
|Flash point||121 °C (250 °F; 394 K)|
|Autoignition temperature||540 °C (1,004 °F; 813 K)|
|LD50||4900 mg/kg (rats, oral)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Anthracene is a solid polycyclic aromatic hydrocarbon 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. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet light.
Coal tar contains around 1.5% anthracene and remains a major source of this material.
In 2010, a strong absorption band of anthracene was observed along a line of sight to a star in the open cluster IC 348, and this may be associated with an intervening molecular cloud. More than 20% of the carbon in the universe may be associated with PAHs, including anthracene.
Commercial anthracene is obtained from coal tar, common impurities being 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.
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. The reversible dimerization and the photochromic properties of anthracenes are the basis of potential applications. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of oxygen.
In general, reduction of anthracene yields 9,10-dihydroanthracene (destroying the aromaticity of the center ring) rather than 1,4-dihydroanthracene (which would destroy the aromaticity of one of the terminal rings). This preference for reduction at the 9 and 10 positions is explained by the fact that aromatic stabilization energy is directly correlated with the number of conjugated pi bonds in an aromatic system. Since 9,10-dihydroanthracene in essence preserves two "benzene" rings (a total of 6 conjugated pi bonds), whereas the 1,4-isomer preserves only one and a half such rings (a total of 5 pi bonds); the latter is not the thermodynamically favorable product. Likewise, electrophilic substitution occurs at the "9" and "10" positions of the center ring.
Anthracene is an organic semiconductor. It is used as a scintillator for detectors of high energy photons, electrons and alpha particles. Plastics, such as polyvinyltoluene, can be doped with anthracene to produce a plastic scintillator that is approximately water-equivalent for use in radiation therapy dosimetry. Anthracene's emission spectrum peaks at between 400 nm and 440 nm.
Anthracene is one of the three components (the other two being potassium perchlorate and sulfur) which are used to produce the black smoke released during a Papal Conclave.
A variety of anthracene derivatives find niche uses. Derivatives having a hydroxyl group are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and naphthols, and hydroxyanthracene (also called anthrol, and anthracenol) are pharmacologically active. Anthracene may also be found with multiple hydroxyl groups, as in 9,10-dihydroxyanthracene.
Unlike many other polycyclic aromatic hydrocarbons (PAH), anthracene is not classified as carcinogenic as listed by OSHA. Anthracene, as many other PAHs, is generated during combustion processes: Exposure to humans happens mainly through tobacco smoke and ingestion of food contaminated with combustion products.
- Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
- Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). New York: D. Van Nostrand Company. p. 81.
- Anthracene in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-22)
- "Properties of Anthracene". http://www.infotherm.com. Wiley Information Services GmbH. Retrieved 2014-06-22.
- Douglas, Bodie E.; Ho, Shih-Ming (2007). Structure and Chemistry of Crystalline Solids. New York: Springer Science+Business Media, Inc. p. 289. ISBN 0-387-26147-8.
- Sigma-Aldrich Co., Anthracene. Retrieved on 2014-06-22.
- "MSDS of Anthracene". http://www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-22.
- Jonathan Lindsey and coworkers. "Anthracene". PhotochemCAD. Retrieved 20 February 2014.
- Iglesias-Groth, S.; Manchado, A.; Rebolo, R.; Gonzalez Hernandez, J. I.; Garcia-Hernandez, D. A.; Lambert, D. L. (May 2010). "A search for interstellar anthracene toward the Perseus anomalous microwave emission region". arXiv:1005.4388. Bibcode:2010MNRAS.407.2157I. doi:10.1111/j.1365-2966.2010.17075.x.
- Hoover, Rachel (February 21, 2014). "Need to Track Organic Nano-Particles Across the Universe? NASA's Got an App for That". NASA. Retrieved February 22, 2014.
- For an example in synthesis of nanosheets refer to: Synthesis of a Covalent Monolayer Sheet by Photochemical Anthracene Dimerization at the Air/Water Interface and its Mechanical Characterization by AFM Indentation; P. Payamyar, K. Kaja, C. Ruiz‐Vargas, A. Stemmer, D. J Murray, C. J Johnson, B. T. King, F. Schiffmann, J. VandeVondele, A. Renn, S. Götzinger, P. Ceroni, A. Schütz, L.‐T. Lee, Z. Zheng, J. Sakamoto, A. D. Schlüter, Adv. Mater 2014, 26, 2052–2058. doi:10.1002/adma.201304705
- Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)2 Kimberly D. M. Charleton, Ernest M. Prokopchuk Journal of Chemical Education 2011 88 (8), 1155-1157 doi:10.1021/ed100843a
- Gerd Collin, Hartmut Höke and Jörg Talbiersky "Anthracene" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a02_343.pub2
- Vatican Radio, Briefing by Fr. Federico Lombardi, 03/13/2013, 1 p.m. CET.
- 1-Hydroxyanthracene NIST datapage
- 2-Hydroxyanthracene NIST datapage
- Wilson, Elizabeth K. (September 27, 2005). "Molecules Take A Walk - Unidirectional motion gives researchers control important for molecular machines, self-assembly". C&EN 83 (40). Retrieved November 5, 2014.
|Wikimedia Commons has media related to Anthracene.|
|Wikisource has the text of the 1879 American Cyclopædia article Anthracene.|
- Image of anthracene crystals
- International Chemical Safety Card 0825
- IARC - Monograph 32
- National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
- European Chemicals Agency - ECHA
- "Anthracene". Encyclopædia Britannica (11th ed.). 1911.