Anthracene
Names | |
---|---|
IUPAC name
Anthracene
| |
Identifiers | |
3D model (
JSmol ) |
|
1905429 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
|
100.003.974 |
EC Number |
|
67837 | |
KEGG | |
PubChem CID
|
|
RTECS number
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C14H10 | |
Molar mass | 178.234 g·mol−1 |
Appearance | Colorless |
Odor | Weak aromatic |
Density | 1.28 g/cm3 (25 °C)[1] 0.969 g/cm3 (220 °C) |
Melting point | 216 °C (421 °F; 489 K)[1] at 760 mmHg |
Boiling point | 341.3 °C (646.3 °F; 614.5 K)[1] at 760 mmHg |
0.022 mg/L (0 °C) 0.044 mg/L (25 °C) 0.29 mg/L (50 °C) 0.00045% w/w (100 °C, 3.9 MPa)[2] | |
Solubility | Soluble in alcohol, (C2H5)2O, acetone, C6H6, CHCl3,[1] CS2[3] |
Solubility in ethanol | 0.76 g/kg (16 °C) 19 g/kg (19.5 °C) 3.28 g/kg (25 °C)[3] |
Solubility in methanol | 18 g/kg (19.5 °C)[3] |
Solubility in hexane | 3.7 g/kg[3] |
Solubility in toluene | 9.2 g/kg (16.5 °C) 129.4 g/kg (100 °C)[3] |
Solubility in carbon tetrachloride | 7.32 g/kg[3] |
log P | 4.56 |
Vapor pressure | 0.01 kPa (125.9 °C) 0.1 kPa (151.5 °C)[4] 13.4 kPa (250 °C)[5] |
Henry's law
constant (kH) |
0.0396 L·atm/mol[6] |
UV-vis (λmax) | 345.6 nm, 363.2 nm[5] |
−129.8×10−6 cm3/mol[7] | |
Thermal conductivity
|
0.1416 W/(m·K) (240 °C) 0.1334 W/(m·K) (270 °C) 0.1259 W/(m·K) (300 °C)[8] |
Viscosity | 0.602 cP (240 °C) 0.498 cP (270 °C) 0.429 cP (300 °C)[8] |
Structure | |
Monoclinic (290 K)[9] | |
P21/b[9] | |
D5 2h[9] | |
a = 8.562 Å, b = 6.038 Å, c = 11.184 Å[9] α = 90°, β = 124.7°, γ = 90°
| |
Thermochemistry[10] | |
Heat capacity (C)
|
210.5 J/(mol·K) |
Std molar
entropy (S⦵298) |
207.5 J/(mol·K) |
Std enthalpy of (ΔfH⦵298)formation |
129.2 kJ/mol |
Std enthalpy of (ΔcH⦵298)combustion |
7061 kJ/mol[5] |
Hazards | |
GHS labelling: | |
[11] | |
Warning | |
H302, H305, H315, H319, H335, H410[11] | |
P261, P273, P305+P351+P338, P501[11] | |
NFPA 704 (fire diamond) | |
Flash point | 121 °C (250 °F; 394 K)[11] |
540 °C (1,004 °F; 813 K)[11] | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
100-149 mg/kg (rats, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Anthracene is a solid
Occurrence and production
Coal tar, which contains around 1.5% anthracene, remains a major source of this material. Common impurities are phenanthrene and carbazole. The mineral form of anthracene is called freitalite and is related to a coal deposit.[14] 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.[15]
Reactions
Reduction
Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]− (M = Li, Na, K). Hydrogenation gives 9,10-
Cycloadditions
Anthracene photodimerizes by the action of UV light:
The
Anthracene also reacts with dienophile singlet oxygen in a [4+2]-cycloaddition (Diels–Alder reaction):
With electrophiles
Chemical
Electrophilic substitution of anthracene occurs at the 9 position. For example, formylation affords
Uses
Anthracene is converted mainly to anthraquinone, a precursor to dyes.[22]
Niche
Anthracene, a wide band-gap
It is also used in wood preservatives, insecticides, and coating materials.[citation needed]
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
A variety of anthracene derivatives find specialized uses. Derivatives having a
Some anthracene derivatives are used as pharmaceutical drugs, including bisantrene, trazitiline, and benzoctamine.
Occurrence
Anthracene, as many other
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. Furthermore, it is readily biodegraded in soil. It is especially susceptible to degradation in the presence of light.[22]
See also
- 9,10-Dithioanthracene, derivative with two thiol groups added to the central ring
- Phenanthrene
- Tetracene
References
- ^ a b c d Haynes, p. 3.28
- ^ Haynes, p. 5.157
- ^ 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. pp. 81.
- ^ Haynes, p. 6.116
- ^ a b c Anthracene in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-22)
- ^ Haynes, p. 5.157
- ^ Haynes, p. 3.579
- ^ a b "Properties of Anthracene". www.infotherm.com. Wiley Information Services GmbH. Archived from the original on 2014-11-01. Retrieved 2014-06-22.
- ^ ISBN 978-0-387-26147-8.
- ^ Haynes, p. 5.41
- ^ a b c d e Sigma-Aldrich Co., Anthracene. Retrieved on 2014-06-22.
- ^ "MSDS of Anthracene". www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-22.
- ^ Lindsey, Jonathan; et al. "Anthracene". PhotochemCAD. Retrieved 20 February 2014.
- ^ Freitalite, Mindat, https://www.mindat.org/min-54360.html
- ^ "Anthracene". American Chemical Society. Retrieved 2022-09-14.
- .
- ISBN 978-0471264187.
- doi:10.1039/a801821i.
- .
- .
- .
- ^
- ^ Zeitler, Alex (2012-06-27) Conformal Coating 101: General Overview, Process Development, and Control Methods. BTW, Inc.
- ^ 1-Hydroxyanthracene. NIST datapage
- ^ 2-Hydroxyanthracene. NIST datapage
Cited sources
- Haynes, William M., ed. (2011). ISBN 978-1439855119.