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Anthracene

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Anthracene
Skeletal formula and numbering system of anthracene
Ball-and-stick model of the anthracene molecule
Anthracene
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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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120-12-7 7pxY
ChEBI CHEBI:35298 7pxY
ChEMBL ChEMBL333179 7pxY
ChemSpider 8111 7pxY
DrugBank DB07372 7pxY
EC number 217-004-5
Jmol-3D images Image
Image
KEGG C14315 7pxY
PubChem Template:Chembox PubChem/format
RTECS number CA9350000
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C14H10
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Appearance Colorless
Odor Weak aromatic
Density 1.28 g/cm3 (25 °C)[1]
0.969 g/cm3 (220 °C)
Melting point Script error: No such module "convert".
at 760 mmHg[1]
Boiling point Script error: No such module "convert".
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]
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]
0.039 L·atm/mol[1]
UV-vismax) 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]
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Crystal structure Monoclinic (290 K)[5]
Space group P21/b[5]
Point group CScript error: No such module "Su".[5]
Lattice constant a = 8.562 Å, b = 6.038 Å, c = 11.184 Å[5]
Lattice constant α = 90°, β = 124.7°, γ = 90°
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210.5 J/mol·K[1][3]
207.5 J/mol·K[1][3]
129.2 kJ/mol[1][3]
7061 kJ/mol[3]
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GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[6]
GHS signal word Warning
H315, H319, H335, H410[6]
P261, P273, P305+351+338, P501[6]
EU classification Irritant Xi Dangerous for the Environment (Nature) N
R-phrases R36/37/38, R50/53
S-phrases S26, S60, S61
NFPA 704

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1
2
1
Flash point Script error: No such module "convert".[6]
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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).
 14pxY verify (what is10pxY/10pxN?)
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]

Occurrence

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.[9] More than 20% of the carbon in the universe may be associated with PAHs, including anthracene.[10]

Production

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.

Reactions

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. The reversible dimerization and the photochromic properties of anthracenes are the basis of potential applications.[11] 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.

Oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate.[12]

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

Uses

Anthracene is converted mainly to anthroquinone, a precursor to dyes.[13]

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.

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.[14]

Derivatives

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)[15][16] 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 OSHA.[17] 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.[18]

See also


References

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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)
  4. ^ a b "Properties of Anthracene". http://www.infotherm.com. Wiley Information Services GmbH. Retrieved 2014-06-22. 
  5. ^ 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. 
  6. ^ a b c d e Sigma-Aldrich Co., Anthracene. Retrieved on 2014-06-22.
  7. ^ a b "MSDS of Anthracene". http://www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-22. 
  8. ^ Jonathan Lindsey and coworkers. "Anthracene". PhotochemCAD. Retrieved 20 February 2014. 
  9. ^ 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". Bibcode:2010MNRAS.407.2157I. arXiv:1005.4388. doi:10.1111/j.1365-2966.2010.17075.x. 
  10. ^ 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. 
  11. ^ For an example in synthesis of nanosheets refer to: Payamyar, P.; Kaja, K.; Stemmer, A.; Murray, D. J; Johnson, C. J; King, B. T.; Schiffmann, F.; VandeVondele, J.; Renn, A.; Götzinger, S.; Ceroni, P.; Schütz, A.; Lee, T.; Zheng, Z.; Sakamoto, J.; Schlüter, A. D. (2014). "Synthesis of a Covalent Monolayer Sheet by Photochemical Anthracene Dimerization at the Air/Water Interface and its Mechanical Characterization by AFM Indentation". Adv. Mater 26: 2052–2058. doi:10.1002/adma.201304705. 
  12. ^ 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
  13. ^ 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
  14. ^ Vatican Radio, Briefing by Fr. Federico Lombardi, 03/13/2013, 1 p.m. CET.
  15. ^ 1-Hydroxyanthracene NIST datapage
  16. ^ 2-Hydroxyanthracene NIST datapage
  17. ^ MSDS
  18. ^ http://www.cie.iarc.fr/htdocs/monographs/vol32/anthracene.html
  19. ^ 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

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