Names | |
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IUPAC names
Anthracene;
Tricyclo[8.4.0.03,8]tetradeca-1,3,5,7,9,11,13-heptaene |
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Identifiers | |
120-12-7 | |
ChEBI | CHEBI:35298 |
ChEMBL | ChEMBL333179 |
ChemSpider | 8111 |
DrugBank | DB07372 |
EC Number | 217-004-5 |
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Jmol interactive 3D | Image Image |
KEGG | C14315 |
PubChem | 8418 |
RTECS number | CA9350000 |
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UNII | EH46A1TLD7 |
Properties | |
C14H10 | |
Molar mass | 178.23 g·mol−1 |
Appearance | Colorless |
Odor | Weak aromatic |
Density | 1.28 g/cm3 (25 °C)[1] 0.969 g/cm3 (220 °C) |
Melting point | 215.76 °C (420.37 °F; 488.91 K) at 760 mmHg[1] |
Boiling point | 339.9 °C (643.8 °F; 613.0 K) at 760 mmHg[1] |
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)[1] |
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Solubility | Soluble in alcohol, (C2H5)2O, acetone, C6H6, CHCl3,[1] CS2[2] |
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)[2] |
Solubility in methanol | 1.8 g/100 g (19.5 °C)[2] |
Solubility in hexane | 0.37 g/100 g[2] |
Solubility in toluene | 0.92 g/100 g (16.5 °C) 12.94 g/100 g (100 °C)[2] |
Solubility in carbon tetrachloride | 0.732 g/100 g[2] |
log P | 4.56[1] |
Vapor pressure | 0.01 kPa (125.9 °C) 0.1 kPa (151.5 °C)[1] 13.4 kPa (250 °C)[3] |
Henry's law
constant (kH) |
0.039 L·atm/mol[1] |
UV-vis (λmax) | 345.6 nm, 363.2 nm[3] |
Thermal conductivity | 0.1416 W/m·K (240 °C) 0.1334 W/m·K (270 °C) 0.1259 W/m·K (300 °C)[4] |
Viscosity | 0.602 cP (240 °C) 0.498 cP (270 °C) 0.429 cP (300 °C)[4] |
Structure | |
Monoclinic (290 K)[5] | |
P21/b[5] | |
C5 2h[5] |
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a = 8.562 Å, b = 6.038 Å, c = 11.184 Å[5]
α = 90°, β = 124.7°, γ = 90°
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Thermochemistry | |
210.5 J/mol·K[1][3] | |
Std molar
entropy (S |
207.5 J/mol·K[1][3] |
Std enthalpy of
formation (ΔfH |
129.2 kJ/mol[1][3] |
Std enthalpy of
combustion (ΔcH |
7061 kJ/mol[3] |
Hazards | |
GHS pictograms | [6] |
GHS signal word | Warning |
H315, H319, H335, H410[6] | |
P261, P273, P305+351+338, P501[6] | |
EU classification (DSD)
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Xi N |
R-phrases | R36/37/38, R50/53 |
S-phrases | S26, S60, S61 |
NFPA 704 | |
Flash point | 121 °C (250 °F; 394 K)[6] |
540 °C (1,004 °F; 813 K)[6] | |
Lethal dose or concentration (LD, LC): | |
LD50 (Median dose)
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4900 mg/kg (rats, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
Infobox references | |
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. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet light.[8]
Contents
Occurrence and production
Coal tar, which contains around 1.5% anthracene, remains a major 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.
It may also occur in the interstellar medium.[9] More than 20% of the carbon in the universe may be associated with PAHs, including anthracene.[10]
Reactions
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]
Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]- (M = Li, Na, K). Hydrogenation gives 9,10-dihydroanthracene, preserving the aromaticity of the two flanking rings.
Chemical oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate.[13]
Anthracene also reacts with dienophile singlet oxygen in a [4+2]-cycloaddition (Diels–Alder reaction):
Uses
Anthracene is converted mainly to anthroquinone, a precursor to dyes.[14]
Niche
Anthracene, a wide band-gap organic semiconductor 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.
It is also used in wood preservatives, insecticides, and coating materials.[citation needed]
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.[15]
Derivatives
A variety of anthracene derivatives find specialized uses. Derivatives having a hydroxyl group are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and naphthols, and hydroxyanthracene (also called anthrol, and anthracenol)[16][17] are pharmacologically active. Anthracene may also be found with multiple hydroxyl groups, as in 9,10-dihydroxyanthracene.
Toxicology
Unlike many other polycyclic aromatic hydrocarbons (PAH), anthracene is not classified as carcinogenic as listed by the U.S. agency OSHA.[18] 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.[19]
See also
References
- ^ a b c d e f g h i j k Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
- ^ a b c d e f Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). New York: D. Van Nostrand Company. p. 81.
- ^ a b c d e f 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)
- ^ a b "Properties of Anthracene". http://www.infotherm.com. Wiley Information Services GmbH. Retrieved 2014-06-22. External link in
|website=
(help) - ^ a b c d 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.
- ^ a b c d e Sigma-Aldrich Co., Anthracene. Retrieved on 2014-06-22.
- ^ "MSDS of Anthracene". http://www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-22. External link in
|website=
(help) - ^ 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.
- ^ Rickborn, Bruce "The retro-Diels-Alder reaction. Part I. C-C dienophiles" Organic Reactions 1998, vol. 52. doi:10.1002/0471264180.or052.01
- ^ Bouas-Laurent, Henri; Desvergne, Jean-Pierre; Castellan, Alain; Lapouyade, Rene "Photodimerization of anthracenes in fluid solution: structural aspects" Chemical Society Reviews (2000), vol. 29, pp. 43-55. doi:10.1039/a801821i
- ^ Kimberly D. M. Charleton, Ernest M. Prokopchuk Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)2 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
- ^ MSDS
- ^ http://www.cie.iarc.fr/htdocs/monographs/vol32/anthracene.html
- ^ 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.
External links
- 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.
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