Anthracene

Anthracene
Skeletal formula and numbering system of anthracene
Ball-and-stick model of the anthracene molecule
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
  • 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
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]
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]
210.5 J/(mol·K)
207.5 J/(mol·K)
129.2 kJ/mol
7061 kJ/mol[5]
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard[11]
Warning
H302, H305, H315, H319, H335, H410[11]
P261, P273, P305+P351+P338, P501[11]
NFPA 704 (fire diamond)
[12]
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 121 °C (250 °F; 394 K)[11]
540 °C (1,004 °F; 813 K)[11]
Lethal dose or concentration (LD, LC):
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).
checkY verify (what is checkY☒N ?)

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 radiation.[13]

  1. ^ a b c d Haynes, p. 3.28
  2. ^ Haynes, p. 5.157
  3. ^ 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.
  4. ^ Haynes, p. 6.116
  5. ^ 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)
  6. ^ Haynes, p. 5.157
  7. ^ Haynes, p. 3.579
  8. ^ a b "Properties of Anthracene". www.infotherm.com. Wiley Information Services GmbH. Archived from the original on 2014-11-01. Retrieved 2014-06-22.
  9. ^ 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 978-0-387-26147-8.
  10. ^ Haynes, p. 5.41
  11. ^ a b c d e Sigma-Aldrich Co., Anthracene.
  12. ^ "MSDS of Anthracene". www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-22.
  13. ^ Lindsey, Jonathan; et al. "Anthracene". PhotochemCAD. Retrieved 20 February 2014.